Sodium hydride → methyl [1-((2R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-{[(4-fluorophenyl)sulfonyl]amino}butyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate

HRID 1036630노트

반응식

HRID 1036630 반응식
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:2]1.[H-].[Na+].[Si:17]([O:24][CH2:25][CH2:26][C@@H:27]1[CH2:29][N:28]1[S:30]([C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1)(=[O:32])=[O:31])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[CH3:14][O:13][C:11](=[O:12])[CH2:10][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:1]([CH2:29][C@H:27]([NH:28][S:30]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[CH2:26][CH2:25][O:24][Si:17]([C:20]([CH3:23])([CH3:21])[CH3:22])([CH3:18])[CH3:19])[CH:2]=1

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 25067325Methyl 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)acetateHCID 58399169(2R)-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1-[(4-fluoro-phenyl)sulfonyl]aziridine

생성물 1

HCID 86655913methyl [1-((2R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-{[(4-fluorophenyl)sulfonyl]amino}butyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]acetate수율 37.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To a cooled solution at 0° C. of methyl 1H-pyrrolo[2,3-b]pyridin-3-ylacetate (1.1 g, 5.8 mmol) in DMF (12 mL) was added 60% NaH in oil (0.26 g, 6.4 mmol, 1.1 equiv.). After a period of 10 min at room temperature, the reaction mixture was cooled to 0° C. and a DMF solution (12 mL) of (2R)-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-1-[(4-fluorophenyl)-sulfonyl]aziridine (2.0 g, 5.8 mmol) was added. The reaction was aged 0.5 h at room temperature and poured over saturated ammonium chloride and ethyl acetate. The organic phase was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by combiflash (hexane to 50% ethyl acetate in hexane) to provide 1.2 g of the title compound.

후처리

  1. waitThe reaction was aged 0.5 h at room temperature
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by combiflash (hexane to 50% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-a603c40d6dda47a2ac6a9d622813d31b
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546422B2

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