Sodium Carbonate → 4-Chloro-2-(imidazo[1,2-a]pyridin-5-yl)phenol

HRID 2203417노트

반응식

HRID 2203417 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17]C)=[C:6]([C:8]2[N:13]3[CH:14]=[CH:15][N:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)[CH:7]=1.B(Br)(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:17])=[C:6]([C:8]2[N:13]3[CH:14]=[CH:15][N:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)[CH:7]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 895442625-(5-Chloro-2-methoxyphenyl)imidazo[1,2-a]pyridine

생성물 1

HCID 1365088014-Chloro-2-(imidazo[1,2-a]pyridin-5-yl)phenol수율 73%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 5-(5-chloro-2-methoxyphenyl)imidazo[1,2-a]pyridine (1.82 g, 7.03 mmol) in dichloromethane (30 mL) at −78° C. was added boron tribromide (1.0 mL, 10.6 mmol). The mixture was allowed to warm to ambient temperature and stirred for 4 h and cooled to 0° C. The reaction mixture was cautiously diluted with water and the pH was adjusted to >7 by the addition of 2 M aqueous sodium carbonate, causing a precipitate to be deposited. The solid was collected by filtration and washed sequentially with water, dichloromethane and diethyl ether to afford 4-chloro-2-(imidazo[1,2-a]pyridin-5-yl)phenol as a colorless solid in 73% yield (1.26 g): 1H NMR (300 MHz, DMSO-d6) δ10.41 (s, 1H), 7.72-7.55 (m, 2H), 7.55-7.28 (m, 4H), 7.06 (d, J=8.4 Hz, 1H), 6.91 (d, J=6.9 Hz, 1H); MS (ES+) m/z 245.0 (M+1), 247.0 (M+1).

후처리

  1. temperaturecooled to 0° C
  2. filtrationThe solid was collected by filtration
  3. washwashed sequentially with water, dichloromethane and diethyl ether

출처 및 근거

ORD 기록
ord-59c6a49d85c3401cb2b6aa2d9be5039a
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365578B2

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