Chloroacetaldehyde → 6-Bromoimidazo[1,2-a]pyridine

HRID 751294Notes

Reaction equation

HRID 751294 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.Cl[CH2:10][CH:11]=O.C(=O)(O)[O-].[Na+]>C(#N)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[CH:11][N:1]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 706222-Amino-5-bromopyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 27955476-Bromoimidazo[1,2-a]pyridineYield 83.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Reflux a solution of 2-amino-5-bromo-pyridine (Maybridge; 1.0 g, 5.78 mmol), 50% 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 (83%) of the subtitled compound as a tan solid. MS (electrospray, m/z) 196.7, 198.7 (M+1). 1H NMR (400 MHz, DMSO-d6) δ 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).

Workup

  1. additionDilute
  2. extractionextract into ethyl acetate

Sources & evidence

ORD record
ord-069c7d4bb27b457280b6c6a1be464f9a
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

Loading…