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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
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HRID 628379 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-87aa8eef9ae5487bbd858bfde371c224
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09309246B2

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