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

HRID 1924764ノート

反応式

HRID 1924764 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-057ea19f58da4c6f959657f344d38851
出典データセット
uspto-grants-2012_05
特許番号
US08178555B2

反応ノート

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