Diisopropylethylamine → 3-Bromo-8-fluoro-7-[2-(triethylsilyloxy)prop-2-yl]imidazo[1,2-alpha]pyridine

HRID 1180222노트

반응식

HRID 1180222 반응식
CCN(C(C)C)C(C)C.FC(F)(F)S([O:15][Si:16]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:17][CH3:18])(=O)=O.[Br:25][C:26]1[N:30]2[CH:31]=[CH:32][C:33]([C:36](O)([CH3:38])[CH3:37])=[C:34]([F:35])[C:29]2=[N:28][CH:27]=1>C(Cl)Cl>[Br:25][C:26]1[N:30]2[CH:31]=[CH:32][C:33]([C:36]([O:15][Si:16]([CH2:17][CH3:18])([CH2:19][CH3:20])[CH2:21][CH3:22])([CH3:38])[CH3:37])=[C:34]([F:35])[C:29]2=[N:28][CH:27]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 674869102-(3-Bromo-8-fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

생성물 1

HCID 695489923-Bromo-8-fluoro-7-[2-(triethylsilyloxy)prop-2-yl]imidazo[1,2-alpha]pyridine수율 101.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Hünig's base (0.44 ml, 3.8 mmol) and triethylsilyl trifluoromethanesulfonate (0.57 ml, 2.6 mmol) were added sequentially to a cold (−78° C.), stirred solution of 2-(3-bromo-8-fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol (637 mg, 2.3 mmol) in CH2Cl2 (13 ml) and the solution warmed to ambient temperature. The mixture was partitioned between CH2Cl2 (50 ml) and water (50 ml) and the organic phase dried over anhydrous MgSO4, filtered through a short plug of silica (eluent CH2Cl2) and concentrated to afford 3-bromo-8-fluoro-7-[2-(triethylsilyloxy)prop-2-yl]imidazo[1,2-α]pyridine (906 mg, quant.): δH (360 MHz, CDCl3) 0.70 (6H, q, J 7.8), 0.99 (9H, t, J 7.8), 1.71 (6H, s), 7.32 (1H, t, J 6.9), 7.59 (1H, s), 7.88 (1H, d, J 7.3).

후처리

  1. customThe mixture was partitioned between CH2Cl2 (50 ml) and water (50 ml)
  2. dry with materialthe organic phase dried over anhydrous MgSO4
  3. filtrationfiltered through a short plug of silica (eluent CH2Cl2)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-efbe2fe973db4c58adc61f645e566020
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279580B2

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