tert-Butanol → tert-Butyl 4-(6-bromo-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate

HRID 2205866ノート

反応式

HRID 2205866 の反応式
C1CCN2C(=NCCC2)CC1.[Br:12][C:13]1[N:18]=[CH:17][C:16]2[CH:19]=[C:20]([C:26]3[CH:27]=[N:28][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:30]=3)[N:21](S(C)(=O)=O)[C:15]=2[CH:14]=1.C(O)(C)(C)C>C1COCC1.O>[Br:12][C:13]1[N:18]=[CH:17][C:16]2[CH:19]=[C:20]([C:26]3[CH:27]=[N:28][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:30]=3)[NH:21][C:15]=2[CH:14]=1

参加物

6

反応物 3

HCID 6386tert-ButanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86706269tert-Butyl 4-(6-bromo-1-(methylsulfonyl)-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate

生成物 1

HCID 86706280tert-Butyl 4-(6-bromo-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate収率 63.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

DBU (0.193 mL, 1.289 mmol) was added to a solution of tert-butyl 4-(6-bromo-1-(methylsulfonyl)-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate (9) (0.517 g, 1.172 mmol) and tert-butanol (0.224 mL, 2.343 mmol) in THF (11.7 mL). The reaction mixture was stirred at 40° C. for 1 hr. It was then diluted with water and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude mixture was adsorbed on silica and purified via Biotage (DCM/EtOAc, 95/5 to 85/15, 25+M column) to afford the title compound as a white solid (271 mg, 58%). 1H NMR (500 MHz, CDCl3) 1.71 (s, 9H), 6.75 (s, 1H), 7.50 (s, 1H), 8.02 (s, 1H), 8.38 (s, 1H), 8.50 (s, 1H), 8.66 (s, 1H).

後処理

  1. extractionthe aqueous layer was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. custompurified via Biotage (DCM/EtOAc, 95/5 to 85/15, 25+M column)

出典と根拠

ORDレコード
ord-ba29c29b62234ba08b2c667cebdb8020
出典データセット
uspto-grants-2016_06
特許番号
US09371319B2

反応ノート

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