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2-Chloro-3-nitropyridine (10.0 g, 63.07 mmol) was dissolved in 500 mL anydrous THF and magnetically stirred at -78 °C. Excess vinylmagnesium bromide (1 M in THF, 200 mL, 200.0 mmol) was added dropwise, after the addition was complete, the solution was allowed to warm to -20 °C. After 16 h, an aqueous solution of saturated ammonium chloride (300 g/L, 150 mL, 841.25 mmol) was added dropwise under vigorous stirring. The resulting suspension was filtered over Hyflo Super Cel medium (calcined) and extracted with EtOAc ( .x. 3). The combined organic fractions were concentrated and automated flash chromatography (CHEXAMPLE 19: 4-(4-(7-Chloro-l-ethyl-l//-pyrrolo[2, 3-c]pyridin-3-yl)pyrimidin-2-ylamino)phenol (Compound70); A solution of 2-chloro-3-nitropyridine (31.5 mmol) in dry THF (200 mL) was cooled to -78°C. Vinylmagnisium bromide (1.0 M in THF, 10OmL) was added dropwise under NExample 19; 4-(4-(7-Chloro-1-ethyl-1H-pyrrolo[2, 3-c]pyridin-3-yl)pyrimidin-2-ylamino)phenol (Compound 70) A solution of 2-chloro-3-nitropyridine (31.5 mmol) in dry THF (200 mL) was cooled to -78° C. Vinylmagnisium bromide (1.0 M in THF, 100 mL) was added dropwise under NTo a solution of 2-chloro-3-nitropyridine (50 g, 315 mmol, 1.0 eq) in THF (1.5 L) was added dropwise vinylmagnesium bromide (1 M in THF, 946.14 mL, 3.00 eq) at -78 °C. After the addition was complete, the mixture was allowed to warm to 25 °C and stirred for 14 h. TLC (petroleum ether: ethyl acetate = 3:1, Rf = 0.25) showed that the reaction was complete. The reaction was quenched with saturated NH4Cl (400 mL) and extracted with EtOAc (500 mL x 3). The combined organic layer was concentrated and the residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 2:1 to 1:1) to give 7-chloropyrrolo[2, 3-c]pyridine (18 g, 118 mmol, 37percent yield) as a yellow solid. 1H NMR (400 MHz CDCl3) = 8.72 (br s, 1H), 8.07 (d, J = 5.6 Hz, 1H), 7.52 (d, J = 5.6 Hz, 1H), 7.46 - 7.44 (m, 1H), 6.66 (t, J = 2.8 Hz, 1H). ESI-MS( m/z): 153.1(M+H)+A solution of 2-chloro-3-nitropyridine (1 g, 6.3 mmol) in dry tetrahydrofuran (100 mL) was treated with vinyl magnesium bromide (60 mL, 60 mmol) at -78 °C in a drop-wise manner under inert atmosphere. The resulting reaction mixture was stirred at the same temperature for 2 hours followed by stirring at -20 °C for 8 hours. The reaction was quenched slowly with aqueous ammonium chloride solution (20 mL), extracted with ethyl acetate (3 x 50 mL) and the combined organic layer dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel (100-200) column chromatography using ethyl acetate and hexane gradient elution to afford 7-chloro-1 H-pyrrolo[2, 3-c]pyridine (0.350 g, 36.45percent).A solution of 2-chloro-3-nitropyridine (1 g, 6.3 mmol) in dry tetrahydrofuran (100 mL) was treated with vinyl magnesium bromide (60 mL, 60 mmol) at -78° C. in a drop-wise manner under inert atmosphere. The resulting reaction mixture was stirred at the same temperature for 2 hours followed by stirring at -20° C. for 8 hours. The reaction was quenched slowly with aqueous ammonium chloride solution (20 mL), extracted with ethyl acetate (3*50 mL) and the combined organic layer dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel (100-200) column chromatography using ethyl acetate and hexane gradient elution to afford 7-chloro-1H-pyrrolo[2, 3-c]pyridine (0.350 g, 36.45percent). Typical procedure for preparing azaindole from nitropyridine: Preparation of 7-chloro-6-azaindole, Precursor 2a, is an example of Step A of Scheme 1. 2-chloro-3-nitropyridine (5.0 g, 31.5 mmol) was dissolved in dry THF (200 mL). After the solution was cooled to -78° C., vinyl magnesium bromide (1.0M in THF, 100 mL) was added dropwise. The reaction temperature was maintained at -78° C. for 1 h, and then at -20° C. for another 12 h before it was quenched by addition of 20percent NH4Cl aqueous solution (150 mL). The aqueous phase was extracted with EtOAc (3.x.150 mL). The combined organic layer was dried over MgSO4, filtered and the filtrate was concentrated in vacuo to give a residue which was purified by silica gel column chromatography (EtOAc/Hexane, 1/10) to afford 1.5 g (31percent) of 7-chloro-6-azaindole, Precursor 2a. 1H NMR (500 MHz, CD3OD) δ7.84 (d, 1H, J=10.7 Hz), 7.55 (dd, 1H, J=10.9, 5.45 Hz), 6.62 (d, 1H, J=5.54 Hz), 4.89 (s, 1H). MS m/z: (M+H)+ calcd for C7H6ClN2: 153.02; found 152.93. HPLC retention time: 0.43 minutes (column A).Preparation of azaindole, Method A: Preparation of 7-Chloro-6-azaindole 1e: 2-Chloro-3-nitropyridine 22e (5.0 g) was dissolved in dry THF (200 ml). After the solution was cooled down to -78° C., an excess of vinyl magnesium bromide (1.0 M in THF, 100 ml) was added. Then, the reaction was left at -20° C. for eight hours before being quenched with 20percent NHTo a 1L three-necked flask under nitrogen is added commercially available vinylmagnesium bromide solution (1 M in THF, 500 mL, 500 mmol). At 0 °C a solution of of 2-chloro-3-nitro- pyridine (25 g, 160 mmol) in THF (100 mL) is added dropwise via addition funnel over 40 minutes. After stirring an additional 40 minutes at 0 °C the reaction is quenched with aqueous saturated NHTo a solution of 2-chloro-3-nitropyridine (5g, 31 .Smmol)) in THF (200mL) at -78°C, was added vinylmagnesium bromide (lOOmL, l.OM in THF) The reaction mixturewas stirred at -20°C for 8 hours, quenched with NHUC1 solution (20percent, 150mL), extractedwith EtOAc, dried over anhydrous NaTo a solution of 2-chloro-3-nitropyridine (1 g) in THF (30mL) cooled at -78°C was slowly added vinylmagnesium bromide (1 M in THF, 20.2ml_). The reaction mixture was warmed up to -30°C and was stirred at -30°C for 30min. Sat. NHTo a solution of 2-chloro-3-nitropyridine (1 g) in THF (30 mL) cooled at ?78° C. was slowly added vinylmagnesium bromide (1 M in THF, 20.2 mL). The reaction mixture was warmed up to ?30° C. and was stirred at ?30° C. for 30 min. Sat. NHA suspension of To a solution of anhydrous THF (35.50 mL) was added 43 (0.71 g, 4.42 mmol). The resulting solution was degassed for 2 h using N2. Hereafter, PdCl2(dppf)·CH2Cl2 (180.50 mg, 0.22 mmol), TMEDA (2.25 mL, 15.03 mmol) and NaBH4 (0.57 g, 15.03 mmol) were added in sequence. The reaction was allowed to continue for 60 h at ambient temperature. The reaction was quenched by slowly pouring the solution in brine. After extraction with EtOAc ( × 3), the combined organic fractions were filtered over Hyflo Super Cel medium (calcined), concentrated in vacuo and purified using automated flash chromatography (EtOAc/MeOH/NH4OH, 960:37.5:2.5) to give 37 (0.39 g; 70.95% yield). Note: This procedure was repeated multiple times using batches of 43 (0.25-2.5 g), giving consistent 65-75% yields at reaction times of 14-60 h 1H NMR (400 MHz, CDCl3) delta 8.75 (s, 1H), 8.04 (d, J = 5.5 Hz, 1H), 7.53-7.46 (m, 1H), 7.43 (t, J = 2.8 Hz, 1H), 6.64 (dd, J = 3.0, 2.1 Hz, 1H).EXAMPLE 25: 7V-(4-Methyl-3-(morpholinosulfonyl)phenyl)-4-(l-propyl-l^-pyrrolo[2, 3-c]pyridin-3- yl)pyrimidin-2-amine (Compound 102); Hydrogenation of 7-chloro-l/f-pyrrolo[2, 3-c]pyridine (10 mmol) was carried out in the presence of Pd-C (10%) in EtOH (5OmL). After stirred at room temperature for 20 hrs, the mixture was filtered through a pad of celite 521. The residue was washed with EtOH several times. The filtrate was evaporated to yield l/f-pyrrolo[2, 3-c]pyridine as brown oil. MS (ESI+) m/z 119.0657 (M+H)+.Example 25; N-(4-Methyl-3-(morpholinosulfonyl)phenyl)-4-(1-propyl-1H-pyrrolo[2, 3-c]pyridin-3-yl)pyrimidin-2-amine (Compound 102) Hydrogenation of 2-Chloro-3-nitropyridine (10.0 g, 63.07 mmol) was dissolved in 500 mL anydrous THF and magnetically stirred at -78 C. Excess vinylmagnesium bromide (1 M in THF, 200 mL, 200.0 mmol) was added dropwise, after the addition was complete, the solution was allowed to warm to -20 C. After 16 h, an aqueous solution of saturated ammonium chloride (300 g/L, 150 mL, 841.25 mmol) was added dropwise under vigorous stirring. The resulting suspension was filtered over Hyflo Super Cel medium (calcined) and extracted with EtOAc ( × 3). The combined organic fractions were concentrated and automated flash chromatography (CH2Cl2/MeOH, 97:3 and then CH2Cl2/MeOH/NH4OH, 980:18.75:1.25) was used to obtain pure 43 (3.87 g, 38% yield). 1H NMR (400 MHz, CDCl3) delta 8.73 (s, 1H), 8.04 (d, J = 5.5 Hz, 1H), 7.53-7.46 (m, 1H), 7.43 (dd, J = 6.2, 3.4 Hz, 1H), 6.64 (dd, J = 3.1, 2.1 Hz, 1H).EXAMPLE 19: 4-(4-(7-Chloro-l-ethyl-l//-pyrrolo[2, 3-c]pyridin-3-yl)pyrimidin-2-ylamino)phenol (Compound70); A solution of 2-chloro-3-nitropyridine (31.5 mmol) in dry THF (200 mL) was cooled to -78C. Vinylmagnisium bromide (1.0 M in THF, 10OmL) was added dropwise under N2. The mixture was stirred at -78C for lhr, followed by -200C for further 8 hrs. The mixture was quenched with 150 mL NH4Cl (20% in H2O) and extracted with EtOAc (3xl50mL). The organic layers were combined, washed with brine, dried on MgSO4 and filtered. The solvent was evaporated and the residue was purified by column chromatography using EtOAc/PE (1:3, v/v) to elute 7- chloro-l/f-pyrrolo[2, 3-c]pyridine as white solid (1.77 g, yield 37%). 1H-NMR (DMSO-J6) delta: 6.63 (d, IH, J= 3.2 Hz, Ar-H), 7.58 (d, IH, J= 5.6 Hz, Ar-H), 7.66 (d, IH, J= 2.8 Hz, Ar-H), 7.90 (d, IH, J= 5.2 Hz, Ar-H). MS (ESI+) m/z 153.0260 (M+H)+.Example 19; 4-(4-(7-Chloro-1-ethyl-1H-pyrrolo[2, 3-c]pyridin-3-yl)pyrimidin-2-ylamino)phenol (Compound 70) A solution of 2-chloro-3-nitropyridine (31.5 mmol) in dry THF (200 mL) was cooled to -78 C. Vinylmagnisium bromide (1.0 M in THF, 100 mL) was added dropwise under N2. The mixture was stirred at -78 C. for 1 hr, followed by -20 C. for further 8 hrs. The mixture was quenched with 150 mL NH4Cl (20% in H2O) and extracted with EtOAc (3×150 mL). The organic layers were combined, washed with brine, dried on MgSO4 and filtered. The solvent was evaporated and the residue was purified by column chromatography using EtOAc/PE (1:3, v/v) to elute To a solution of 2-chloro-3-nitropyridine (50 g, 315 mmol, 1.0 eq) in THF (1.5 L) was added dropwise vinylmagnesium bromide (1 M in THF, 946.14 mL, 3.00 eq) at -78 C. After the addition was complete, the mixture was allowed to warm to 25 C and stirred for 14 h. TLC (petroleum ether: ethyl acetate = 3:1, Rf = 0.25) showed that the reaction was complete. The reaction was quenched with saturated NH4Cl (400 mL) and extracted with EtOAc (500 mL x 3). The combined organic layer was concentrated and the residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 2:1 to 1:1) to give A solution of 2-chloro-3-nitropyridine (1 g, 6.3 mmol) in dry tetrahydrofuran (100 mL) was treated with vinyl magnesium bromide (60 mL, 60 mmol) at -78 C in a drop-wise manner under inert atmosphere. The resulting reaction mixture was stirred at the same temperature for 2 hours followed by stirring at -20 C for 8 hours. The reaction was quenched slowly with aqueous ammonium chloride solution (20 mL), extracted with ethyl acetate (3 x 50 mL) and the combined organic layer dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel (100-200) column chromatography using ethyl acetate and hexane gradient elution to afford 7-chloro-1 H-pyrrolo[2, 3-c]pyridine (0.350 g, 36.45%).1H NMR (400 MHz, CHCI3-cf): delta 8.04 (d, J=5.46 Hz, 1 H), 7.50 (dd, J=5.46, 0.75 Hz, 1 H) 7.43 (dd, J=3.1 1 , 2.54 Hz, 1 H), 6.64 (dd, J=3.14, 2.07 Hz, 1 H). MS: 152.98 (M+).A solution of 2-chloro-3-nitropyridine (1 g, 6.3 mmol) in dry tetrahydrofuran (100 mL) was treated with vinyl magnesium bromide (60 mL, 60 mmol) at -78 C. in a drop-wise manner under inert atmosphere. The resulting reaction mixture was stirred at the same temperature for 2 hours followed by stirring at -20 C. for 8 hours. The reaction was quenched slowly with aqueous ammonium chloride solution (20 mL), extracted with ethyl acetate (3*50 mL) and the combined organic layer dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel (100-200) column chromatography using ethyl acetate and hexane gradient elution to afford Typical procedure for preparing azaindole from nitropyridine: Preparation of Preparation of azaindole, Method A: Preparation of 7-Chloro-6-azaindole 1e: 2-Chloro-3-nitropyridine 22e (5.0 g) was dissolved in dry THF (200 ml). After the solution was cooled down to -78 C., an excess of vinyl magnesium bromide (1.0 M in THF, 100 ml) was added. Then, the reaction was left at -20 C. for eight hours before being quenched with 20% NH4Cl (150 ml). The aqueous phase was extracted with EtOAc (3×150 ml). The combined organic layer was dried over MgSO4. After filtration and concentration, the crude product was purified by silica gel column chromatography to afford 1.5 g of To a 1L three-necked flask under nitrogen is added commercially available vinylmagnesium bromide solution (1 M in THF, 500 mL, 500 mmol). At 0 C a solution of of 2-chloro-3-nitro- pyridine (25 g, 160 mmol) in THF (100 mL) is added dropwise via addition funnel over 40 minutes. After stirring an additional 40 minutes at 0 C the reaction is quenched with aqueous saturated NH4Cl solution and extracted with EtOAc. The combined organic layers are dried over MgS04, filtered and concentrated in vacuo. The crude material is passed through a plug of silica gel with CH2Cl2/heptanes (33%) as eluant to give a solid that is recrystallized from CH2Cl2/heptanes to deliver 6.9 g (28%) of the titled product as a beige solid mp 182- 185 0 C. 1H NMR (CDCI3) delta 8.60 (br s, 1H), 8.05 (m, 1H), 7.50 (m, 1H), 7.42 (m, 1H), 6.64 (m, 1H). LCMS m/z: 153 (M+H).To a solution of 2-chloro-3-nitropyridine (5g, 31 .Smmol)) in THF (200mL) at -78C, was added vinylmagnesium bromide (lOOmL, l.OM in THF) The reaction mixturewas stirred at -20C for 8 hours, quenched with NHUC1 solution (20%, 150mL), extractedwith EtOAc, dried over anhydrous Na2SC>4 and concentrated. The residue was purified byflash chromatography, eluent EtOAc/hexane (1:5), to afford the title compound 259 (1.23g, 26% yield) as a white solid FZ. Zhang, et al.. J. Ore. Chem., 2002. 67. 2345-23471. MS(m/z): 153.1(M+H) (found).Preparation of To a solution of 2-chloro-3-nitropyridine E-I (20 g, 126 mmol, 1 eq.) in anhydrous TEtaF (800 mL) cooled to -78 0C was added a solution of vinyl magnesium bromide (400 mL of a 1.0 M solution in TEtaF, 400 mmol, 3.2 eq.) by cannula. The mixture was stirred for 6 hours while allowing the mixture to slowly warm to -15 0C. After this period, a solution of saturated aqueous NH4Cl was added, followed by the addition of H2O, and the mixture was extracted with ethyl acetate three times. The combined organic phases were concentrated onto Celite (trade name) and the material was subjected to silica gel chromatography ({CHCI3 (90%), CH3OH (10%), concentrated aqueous NH4OH (1%)} : CHCl3) to provide Compound E-2: LCMS m/e 153 (M+H); 1H NMR (400 MHz, Methanol-d4)deltappm 6.64 (d, J=3.O3 Hz, 1 H), 7.56 (d, J=5.56 Hz, 1 H), 7.58 (d, J=3.07 Hz, 1 H), 7.86 (d, J=5.56 Hz, 1 H).To a solution of 2-chloro-3-nitropyridine (1 g) in THF (30mL) cooled at -78C was slowly added vinylmagnesium bromide (1 M in THF, 20.2ml_). The reaction mixture was warmed up to -30C and was stirred at -30C for 30min. Sat. NH4CI was added and the mixture was extracted with EA twice. The combined org. layers were dried (Na2S04) and evaporated in vacuo. CC (Biotage, SNAP 50g cartridge, solvent A: Hept; solvent B: EA; gradient in %B: 8 for 4CV, 8 to 66 over 10CV, 66 for 2CV) afforded 353mg of rosa solid. LC-MS (B): tR = 0.47 min; [M+H]+: 153.22.To a solution of 2-chloro-3-nitropyridine (1 g) in THF (30 mL) cooled at -78 C. was slowly added vinylmagnesium bromide (1 M in THF, 20.2 mL). The reaction mixture was warmed up to -30 C. and was stirred at -30 C. for 30 min. Sat. NH4Cl was added and the mixture was extracted with EA twice. The combined org. layers were dried (Na2SO4) and evaporated in vacuo. CC (Biotage, SNAP 50 g cartridge, solvent A: Hept; solvent B: EA; gradient in % B: 8 for 4CV, 8 to 66 over 10CV, 66 for 2CV) afforded 353 mg of rosa solid. LC-MS (B): tR=0.47 min; [M+H]+: 153.22.To a solution of 2-chloro-3-nitropyridine in anhydrous THF, a 1 mol/L solution of vinylmagnesium bromide tetrahydrofuran was added dropwise at -40 C for about 30 minutes, and the reaction was allowed to gradually rise to room temperature for 16 hours. After completion of the reaction, the mixture was cooled, and a saturated aqueous solution of ammonium chloride was added, and the mixture was combined with ethyl acetate. The ethyl acetate phase was combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate Elution with ethyl acetate / petroleum ether gradient 10-30% to give The Example B207 7- (4-Butylbenzyl)-1H-pyrrolo[2, 3-c]pyridine The The compound of Example B205 (800 mul, 0.3 mmol) was added to a solution of 1-chloropyrrolopyridine (19.4 mg, 0.127 mmol), which was synthesised from 2-chloro-3-aminopyridine according to the method of H07-165, 708A, and dichloro(diphenylphosphinopropane)nickel (6.9 mg, 0.013 mmol) in tetrahydrofuran (1 ml) under ice-cooling, and the mixture was stirred while'heating under reflux for 4 hours. After allowing the mixture to cool to room temperature, ethyl acetate was added thereto. The resulting mixture was washed with a saturated aqueous ammonium chloride solution and saturated brine, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (7.1 mg). 1H-NMR(CDCl3) delta (ppm): 0.91(3H, t), 1.31-1.37(2H, m), 1.55-1.59(2H, m), 2.58(2H, t), 4.44(2H, s), 6.50(1H, d), 7.12(2H, d), 7.18(1H, d), 7.22(2H, d), 7.45(1H, d), 8.21(1H, d)