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

HRID 628293ノート

反応式

HRID 628293 の反応式
[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

参加物

5

反応物 3

HCID 795Imidazole2 回HCID 28928tert-Butyldimethylsilyl chloride2 回HCID 118159445(1-benzyl-5-chloro-1H-pyrrolo[3,2-b]pyridin-2-yl)methanol

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-fb24d47e80674deb96dd2b23453afd44
出典データセット
uspto-grants-2016_04
特許番号
US09309246B2

反応ノート

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