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Sodium hydride → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((2-(pentafluoroethyl)-1,3-thiazol-4-yl) methoxy)pyridin-2(1H)-one

HRID 2203107
ノート
印刷プレビュー

反応式

HRID 2203107 の反応式
[H-].[Na+].[F:3][C:4]([F:16])([C:9]1[S:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=1)[C:5]([F:8])([F:7])[F:6].Br[C:18]1[CH:23]=[CH:22][N:21]([C:24]2[CH:25]=[CH:26][C:27]3[N:31]=[C:30]([CH:32]4[CH2:34][CH2:33]4)[N:29]([CH3:35])[C:28]=3[CH:36]=2)[C:20](=[O:37])[CH:19]=1>CC(N(C)C)=O>[CH:32]1([C:30]2[N:29]([CH3:35])[C:28]3[CH:36]=[C:24]([N:21]4[CH:22]=[CH:23][C:18]([O:15][CH2:14][C:12]5[N:13]=[C:9]([C:4]([F:3])([F:16])[C:5]([F:8])([F:7])[F:6])[S:10][CH:11]=5)=[CH:19][C:20]4=[O:37])[CH:25]=[CH:26][C:27]=3[N:31]=2)[CH2:33][CH2:34]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 54209966(2-(Perfluoroethyl)thiazol-4-yl)methanolHCID 896908634-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

生成物 1

HCID 896912031-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((2-(pentafluoroethyl)-1,3-thiazol-4-yl) methoxy)pyridin-2(1H)-one収率 5.9%

試薬・触媒・溶媒 1

HCID 31374
Dimethylacetamide
溶媒

反応条件

温度
0 °C

実験手順

NaH (60% in oil, 51.5 mg) was added to a solution of (2-(perfluoroethyl)thiazol-4-yl)methanol (300 mg) in DMA (5 ml) at 0° C. After being stirred at 0° C. for 30 min, 4-bromo-1-(2-cyclopropyl-1-methyl-1H-benzo[d]imidazol-6-yl)pyridin-2(1H)-one (295 mg) was added to the reaction mixture. The mixture was stirred at 120° C. under N2 atmosphere for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc), followed by crystallization from EtOH-water to give the title compound (25 mg) as a white solid.

後処理

  1. stirringThe mixture was stirred at 120° C. under N2 atmosphere for 1 h
  2. customThe mixture was quenched with water
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with water and brine successively
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by NH silica gel column chromatography (hexane/EtOAc)
  9. customfollowed by crystallization from EtOH-water

出典と根拠

ORDレコード
ord-3378319c6142478eb3ad1d89d892dbdd
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09365540B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート