Sodium hydride → 2,2-Dimethyl-propionic acid 5-bromo-3-(4-dimethylamino-benzyl)-pyrazolo[3,4-b]pyridin-1-ylmethyl ester

HRID 1865645노트

반응식

HRID 1865645 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=3)=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[C:23]([O:29][CH2:30]Cl)(=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25].[Cl-].[NH4+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]([CH3:19])[CH3:20])=[CH:14][CH:13]=3)=[N:9][N:8]([CH2:30][O:29][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:5]2=[N:6][CH:7]=1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 87885Chloromethyl pivalateHCID 178482750HCID 178482750, 화합물

생성물 1

HCID 686621972,2-Dimethyl-propionic acid 5-bromo-3-(4-dimethylamino-benzyl)-pyrazolo[3,4-b]pyridin-1-ylmethyl ester수율 77%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

[4-(5-Bromo-1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-phenyl]-dimethyl-amine (500 mg, 1.51 mmol) and N,N-dimethylformamide (40 ml) was stirred at room temperature. Sodium hydride (60%, 121 mg, 3.03 mmol) was added to the mixture, and the reaction mixture was stirred for 30 minutes. Chloromethyl pivalate (0.44 ml, 3.05 mmol) was added, and the reaction mixture was stirred for 1.5 hours at room temperature. Saturated aqueous ammonium chloride solution was added and the mixture extracted with dichloromethane. The crude material was purified by flash chromatography (0 to 100% ethyl acetate in hexanes) to give 517 mg (77%) of 2,2-dimethyl-propionic acid 5-bromo-3-(4-dimethylamino-benzyl)-pyrazolo[3,4-b]pyridin-1-ylmethyl ester. MS m/z 445.2, 447.2 (M+H+).

후처리

  1. stirringthe reaction mixture was stirred for 1.5 hours at room temperature
  2. extractionthe mixture extracted with dichloromethane
  3. customThe crude material was purified by flash chromatography (0 to 100% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-f6b6bce3c05543d78ba1fb344eb2b6f7
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07626021B2

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