Water → N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide

HRID 1924764노트

반응식

HRID 1924764 반응식
[Br:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([NH:11][C:12](=[O:31])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:30])([CH3:29])[CH2:20][O:21][Si](C(C)(C)C)(C)C)=[CH:15][CH:14]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([NH:11][C:12](=[O:31])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:29])([CH3:30])[CH2:20][OH:21])=[CH:15][CH:14]=3)=[N:10][C:5]2=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 58015371N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)benzamide

생성물 1

HCID 58015383N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-(5-bromothiazolo[5,4-b]pyridin-2-yl)-4-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)benzamide (2E, 1.9 g, 1.0 equivalent) was dissolved in THF (0.4 M). Cooled mixture in ice bath, and followed by a slow addition of TBAF (1.0M THF solution, 6.5 equivalents). After addition, mixture was warmed to room temperature and then heated to 60° C. for 3 h. After stirring, water was added and followed by extraction with EtOAc twice. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by chromatography (SiO2, gradient of 1 to 5% MeOH/CH2Cl2) to give 2F (60%) as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.26 (s, 6H) 3.48 (s, 2H) 4.77 (br. s., 1H) 7.57 (d, J=8.59 Hz, 2H) 7.72 (d, J=8.34 Hz, 1H) 8.05-8.16 (m, 3H) 13.08 (s, 1H); ESI-MS: m/z 406.0 (M+H)+.

후처리

  1. temperatureCooled mixture in ice bath
  2. additionAfter addition, mixture
  3. temperatureheated to 60° C. for 3 h
  4. extractionfollowed by extraction with EtOAc twice
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography (SiO2, gradient of 1 to 5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-057ea19f58da4c6f959657f344d38851
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178555B2

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