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Home> Encyclopedia >Agrochemical Intermediates>Organic Intermediate>Pharmaceutical Intermediates
6-Bromoimidazo[1,2-a]pyridine structure
6-Bromoimidazo[1,2-a]pyridine structure

6-Bromoimidazo[1,2-a]pyridine

Iupac Name:6-bromoimidazo[1,2-a]pyridine
CAS No.: 6188-23-4
Molecular Weight:197.035
Modify Date.: 2022-11-29 02:20
Introduction:

(1)To a solution of 5-bromopyridin-2-amine (10.0 g, 57.7 mmol) in EtOH/HThe scheme above describes the synthesis of a compound of the invention. A substituted pyridine such as compound 1-1 is reacted with 2-chloroacetaldehyde, resulting in the halogenated imidazopyridine compound 1-2.j0554] The scheme above describes the synthesis of a compound of the invention. A substituted pyridine such as compound 1-1 is reacted with 2-chloroacetaldehyde, resulting in the halogenated imidazopyridine compound 1-2. Compound 1-2 is coupled to a benzoxazolyl boronic acid ester in Suzuki conditions to produce compound 1-4. Further derivatization of compound 1-4 using, for example, NBS, DMF results in halogenation of the imidazopyridine moiety, which is then further reacted in an additional Suzuki coupling using pyridine boronic acid to result in compound 1-6.2-Amino-5-bromopyridine (Aldrich, 18.8 g, 108.7 mmol), chloroacetaldehyde (34 mL of 50percent solution in water, 217.4 mmol), NaHCOReflux a solution OF 2-AMINO-5-BROMO-PYRIDINE (Maybridge; 1.0 g, 5.78 mmol), 50percent aqueous chloroacetaldehyde (2 mL, 12.7 mmol) in acetonitrile (100 mL) for 14 h. Dilute the reaction with saturated aqueous sodium bicarbonate and extract into ethyl acetate. Flash chromatography using appropriate ethyl acetate/hexane mixtures gives 0.95 g (83percent) of the subtitled compound as a tan solid. MS (electrospray, m/z) 196.7, 198.7 (M+1). 1H NMR (400 MHz, DMSO-d6) 8 8.9 (d, J= 1. 5 Hz, 1H), 7.90 (s, 1H), 7.58 (d, J = 1.5 Hz, 1H), 7.53 (d, J = 9. 2 HZ, 1H), 7.29 (dd, J = 9. 2, 2 HZ, 1H).To a stirred solution of 5-bromo-pyridin-2-amine (5 g, 28.9 mmol) and sodium acetate (4.0 g, 48.76 mmol) in 100 mL of 60 percent ethanol in water, was added a refluxed solution of sodium acetate (2.0 g, 24.38 mmol) followed by 2-chloro-1 , 1 -dimethoxyethane (6.66 g, 53.5 mmol) in concentrated hydrochloric acid (1 .0 mL) in water (6 mL) and the reaction mass was refluxed for 2.5 h. The solvent was removed, residue obtained was diluted with cold water and pH adjusted to neutral (~7) with saturated sodium bicarbonate solution. The reaction mixture was extracted with ethyl acetate (2x100 mL), washed with water (2x100 mL) and brine (2x100 mL) and dried over anhydrous sodium sulphate. The crude material obtained was purified by trituration using 2 percent ethyl acetate in petroleum ether. Yield: 3.6 g (64.28 percent);

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1. Names and Identifiers
1.1 Name
6-Bromoimidazo[1,2-a]pyridine
1.2 Synonyms

6- BROMINE IMIDAZOLYL [ 1,2-A ] PYRIDINE 6-BroMo IMidazole[1,2-a]Pyridine 6-Bromoimidazo[1,2-a]pyri... 6-BroMoiMidazolo[1,2-a]pyridine 6-BROMO-INIDAZO[1,2-A]-PYRIDINE BUTTPARK 154\50-43 IMidazo[1,2-a]pyridine, 6-broMo-

1.3 CAS No.
6188-23-4
1.4 CID
2795547
1.5 EINECS(EC#)
1592732-453-0
1.6 Molecular Formula
C7H5BrN2 (isomer)
1.7 Inchi
InChI=1S/C7H5BrN2/c8-6-1-2-7-9-3-4-10(7)5-6/h1-5H
1.8 InChIkey
FXPMFQUOGYGTAM-UHFFFAOYSA-N
1.9 Canonical Smiles
C1=CC2=NC=CN2C=C1Br
1.10 Isomers Smiles
C1=CC2=NC=CN2C=C1Br
2. Properties
2.1 Density
1.69
2.1 Melting point
76-78℃
2.1 Boiling point
165 °C(Press: 1.5 Torr)
2.1 Refractive index
1.688
2.1 Precise Quality
195.96400
2.1 PSA
17.30000
2.1 logP
2.09680
2.1 Storage
Ambient temperatures.
2.2 Chemical Properties
White crystalline powder 6-Bromoimidazo[1,2-a]pyridineSupplier
2.3 Color/Form
Yellow to Brown Solid
2.4 pKa
5.10±0.50(Predicted)
2.5 Water Solubility
slightly soluble in water.
3. Safety and Handling
3.1 Hazard Codes
Xn
3.1 Risk Statements
R22;R36/37/38
3.1 Safety Statements
S22;S26;S36/37/39
3.1 Hazard Class
IRRITANT
3.1 Hazard Declaration
H301
3.1 RIDADR
NONH for all modes of transport
3.1 Caution Statement
P261, P264, P270, P271, P280, P301+P310, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501
3.1 WGK Germany
3
4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H302 Harmful if swallowed

H315 Causes skin irritation

H319 Causes serious eye irritation

H335 May cause respiratory irritation

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

7. Other Information
7.0 Usage
It is used in organic syntheses and as pharmaceutical intermediates. The best results were obtained with lactams that could be introduced on the 6-bromoimidazo[1,2-a]pyridine. 1,2-dihydro-5-imidazo [1,2-a]pyridin-6-yl-6-methyl-2-oxo-3-pyridinecarbonitrile hydrochloride monohydrate 6 was synthesized in 5 steps from 6-bromoimidazo[1,2-a] pyridine using [2- 14 C] cyanoacetamide as the source of the radiolabel.
8. Computational chemical data
  • Molecular Weight: 197.035g/mol
  • Molecular Formula: C7H5BrN2
  • Compound Is Canonicalized: True
  • XLogP3-AA: 2.5
  • Exact Mass: 195.96361
  • Monoisotopic Mass: 195.96361
  • Complexity: 129
  • Rotatable Bond Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Topological Polar Surface Area: 17.3
  • Heavy Atom Count: 10
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADcYBjAAAAEAAAAAAAAAAAAAAAAWAAAAAsAAAAAAAAAFgB4AAAHABAAAABqADBEwQ9sJ8MGACgADJnZACCgC0xEqQJ2CA4dLiIaOLAmZGUIAhogALIyjYQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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