Imidazole → 1-benzyl-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-pyrrolo[3,2-b]pyridine

HRID 628293노트

반응식

HRID 628293 반응식
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[CH2:14]([N:21]1[C:29]2[C:24](=[N:25][C:26]([Cl:30])=[CH:27][CH:28]=2)[CH:23]=[C:22]1[CH2:31][OH:32])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[CH2:14]([N:21]1[C:29]2[C:24](=[N:25][C:26]([Cl:30])=[CH:27][CH:28]=2)[CH:23]=[C:22]1[CH2:31][O:32][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

참가 물질

5

반응물 3

HCID 795Imidazole2회HCID 28928tert-Butyldimethylsilyl chloride2회HCID 118159445(1-benzyl-5-chloro-1H-pyrrolo[3,2-b]pyridin-2-yl)methanol

생성물 1

HCID 1235320351-benzyl-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-pyrrolo[3,2-b]pyridine수율 92%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-Butyldimethylsilyl chloride (0.12 g, 0.81 mmol) and 1H-imidazole (60. mg, 0.88 mmol) were added to a solution of (1-benzyl-5-chloro-1H-pyrrolo[3,2-b]pyridin-2-yl)methanol (0.20 g, 0.73 mmol, from Step 2) in DCM (10 mL) After stirring for 4 hours, additional tert-butyldimethylsilyl chloride (33 mg, 0.22 mmol) and 1H-imidazole (15 mg, 0.22 mmol) were added and the reaction was continued for one hour. The mixture was filtered and the filtrate was concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-10% EtOAc in hexanes to afford a white solid (0.26 g, 92%).

후처리

  1. waitthe reaction was continued for one hour
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe product was purified by flash chromatography
  5. washeluting with a gradient from 0-10% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-fb24d47e80674deb96dd2b23453afd44
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309246B2

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