General procedure: Aminoacetaldehyde dimethylacetal (3.0 eq.) was added to a solution of bromobenzaldehyde13b or 13c (1.0 eq.) in toluene (30 mL). Each reaction mixture was refluxed (Dean–Stark apparatus)at 120 °C. After consumption of the starting material, each reaction mixture was concentrated todryness, then dissolved in conc. H2SO4 (2 mL) and added to a cold solution of P2O5 in conc. H2SO4(0.5 mL). Each reaction mixture was heated at 160 °C for 30 min, allowed to cool to RT, neutralizedwith NaOH (10 M), extracted with EtOAc, and concentrated to dryness. Each residue was subjected toFCC to afford 6-bromoisoquinoline (14b, 30 mg, 0.14 mmol, 14percent) and 7-bromoisoquinoline (14c, 99 mg, 0.47 mmol, 22percent) [20, 21]. Ethylchloroformate (1.0 eq.) was added to a solution of isoquinoline 14b or14c (1.0 eq.) in DCM at 0 °C and stirred at the same temperature for 30 min, followed by additionof 2-trimethylsilylthiazole (1.0 eq.). Each reaction mixture was stirred at RT for 3 h, concentratedto dryness, and each residue was subjected to FCC. Each product was dissolved in benzene (5 mL), o-chloranil (1.0 eq.) was added, and each reaction mixture was refluxed for 5 h. Each reaction mixturewas diluted with 5percent NaOH (10 mL), extracted with DCM, and concentrated to dryness. Each reactionmixture residue was subjected to FCC to afford the products 9b and 9c.Compound C (21.90 g, 38.93 mmol) and Compound E (8.1 g, 38.93 mmol) were completely dissolved in 300 ml of tetrahydrofuran in a 500 ml round-bottomed flask under nitrogen atmosphere and then 2M aqueous potassium carbonate solution (150 ml)And tetrakis- (triphenylphosphine) palladium (1.34 g, 1.16 mmol) was added thereto, followed by heating and stirring at 75C for 3 hours. The temperature was lowered to room temperature (23 ± 5 C), the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (150 ml) to prepare Compound 3 (11.0 g, 50%).Under nitrogen protection conditions, Add 78.6 g (0.58 mol) of anhydrous zinc chloride to the three-necked bottle, tetrahydrofuran800mL, Lower the temperature of the reaction system to 0 C, 480 mL (0.96 mol) of isopropylmagnesium chloride was added dropwise.Insulation stirring a half smallTime. Then, 3.5 g (1 mol%) of bisphenylphosphinoferrocene palladium dichloride was added.Stir for 15 minutes, 100 g (0.48 mol) of
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