Water → 4-[5-(2,6-diethyl-phenyl)-1-(1-propyl-butyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 472052노트

반응식

HRID 472052 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:22]3[C:17](=[CH:18][N:19]=[C:20]([C:23]4[C:28]([CH2:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=4[CH2:31][CH3:32])[CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH:36]([CH2:40][CH2:41][CH3:42])[CH2:37][CH2:38][CH3:39].O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[C:22]3[C:17](=[CH:18][N:19]=[C:20]([C:23]4[C:28]([CH2:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=4[CH2:31][CH3:32])[CH:21]=3)[N:16]([CH:36]([CH2:40][CH2:41][CH3:42])[CH2:37][CH2:38][CH3:39])[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 704604-BromoheptaneHCID 671525864-[5-(2,6-Diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 671525954-[5-(2,6-diethyl-phenyl)-1-(1-propyl-butyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of the 4-[5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (120 mg, 0.30 mmol) in DMF (4 mL), NaH (60 wt % suspension in mineral oil, 36 mg, 0.89 mmol) is added followed by 4-bromoheptane (159 mg, 0.89 mmol). The mixture is stirred for 40 h at room temperature. The mixture is poured to water (10 mL), and the product is extracted with EtOAc. The combined organic extracts are washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Chromatography of the residue affords 4-[5-(2,6-diethyl-phenyl)-1-(1-propyl-butyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as colorless oil.

후처리

  1. extractionthe product is extracted with EtOAc
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d9f1e05486f34a4f8609b5c503d5cf7c
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633193B2

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