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

HRID 751294노트

반응식

HRID 751294 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  1. additionDilute
  2. extractionextract into ethyl acetate

출처 및 근거

ORD 기록
ord-069c7d4bb27b457280b6c6a1be464f9a
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405299B2

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