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Cesium carbonate → 3-({[tert-Butyl(diphenyl)silyl]oxy}methyl)benzyl 1-[3-({[tert-butyl(diphenyl)sily]oxy}methyl)benzyl]-5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylate

HRID 628379
ノート
印刷プレビュー

反応式

HRID 628379 の反応式
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:11]([OH:13])=[O:12])[NH:10][C:5]2=[CH:4][CH:3]=1.[C:14]([O-:17])([O-])=O.[Cs+].[Cs+].[C:20]([Si:24]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45]Cl)[CH:40]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C>[Si:24]([O:17][CH2:14][C:43]1[CH:44]=[C:39]([CH:40]=[CH:41][CH:42]=1)[CH2:38][N:10]1[C:5]2[C:6](=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:8]=[C:9]1[C:11]([O:13][CH2:45][C:41]1[CH:42]=[CH:43][CH:44]=[C:39]([CH2:38][O:37][Si:24]([C:20]([CH3:23])([CH3:21])[CH3:22])([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:40]=1)=[O:12])([C:20]([CH3:23])([CH3:21])[CH3:22])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 116655855-chloro-1H-pyrrolo(3,2-b)pyridine-2-carboxylic acidHCID 220737533-(t-Butyldiphenylsiloxymethy)benzyl chloride

生成物 1

HCID 1317353483-({[tert-Butyl(diphenyl)silyl]oxy}methyl)benzyl 1-[3-({[tert-butyl(diphenyl)sily]oxy}methyl)benzyl]-5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylate

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

5-Chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid (0.803 g, 4.08 mmol, from Example 99, Step 1) in DMF (20 mL) was treated with Cs2CO3 (4.0 g, 12 mmol), followed by the addition of tert-butyl{[3-(chloromethyl)benzyl]oxy}diphenylsilane (3.9 g, 9.9 mmol, from Step 2). After stirring overnight, the crude reaction mixture was partitioned between water and ethyl acetate and the aqueous layer was extracted with an additional two portions of ethyl acetate. The combined organic extracts were washed sequentially with water and brine, dried over sodium sulfate, filtered and concentrated. The product was purified by flash chromatography, eluting with a slow gradient from 0-20% EtOAc/hexanes. Yield: (2.18 g, 58%).

後処理

  1. customthe crude reaction mixture
  2. customwas partitioned between water and ethyl acetate
  3. extractionthe aqueous layer was extracted with an additional two portions of ethyl acetate
  4. washThe combined organic extracts were washed sequentially with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by flash chromatography
  9. washeluting with a slow gradient from 0-20% EtOAc/hexanes

出典と根拠

ORDレコード
ord-87aa8eef9ae5487bbd858bfde371c224
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09309246B2

反応ノート

読み込み中…

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