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Water → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-(trifluoromethyl)-2-thienyl)methoxy)pyridin-2(1H)-one

HRID 2203102
ノート
印刷プレビュー

反応式

HRID 2203102 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH2:8][OH:9])[S:6][CH:7]=1.[H-].[Na+].Br[C:15]1[CH:20]=[CH:19][N:18]([C:21]2[CH:22]=[CH:23][C:24]3[N:28]=[C:27]([CH:29]4[CH2:31][CH2:30]4)[N:26]([CH3:32])[C:25]=3[CH:33]=2)[C:17](=[O:34])[CH:16]=1.O>CC(N(C)C)=O>[CH:29]1([C:27]2[N:26]([CH3:32])[C:25]3[CH:33]=[C:21]([N:18]4[CH:19]=[CH:20][C:15]([O:9][CH2:8][C:5]5[S:6][CH:7]=[C:3]([C:2]([F:10])([F:1])[F:11])[CH:4]=5)=[CH:16][C:17]4=[O:34])[CH:22]=[CH:23][C:24]=3[N:28]=2)[CH2:30][CH2:31]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

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 896902462-Thiophenemethanol, 4-(trifluoromethyl)-HCID 896908634-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

生成物 1

HCID 896909571-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-(trifluoromethyl)-2-thienyl)methoxy)pyridin-2(1H)-one収率 15%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
120 °C

実験手順

To a solution of (4-(trifluoromethyl)thiophen-2-yl)methanol (50 mg) in DMA (2 ml) was added NaH (60% in oil, 18.3 mg) at room temperature, and the mixture was stirred for 30 min. 4-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (79 mg) was added to the mixture, and the mixture was heated at 120° C. for 30 min under microwave irradiation. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed with saturated NaHCO3 solution and brine successively, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (EtOAc/MeOH), followed by crystallized from hot EtOAc to give the title compound (15.3 mg) as pale yellow crystals.

後処理

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with saturated NaHCO3 solution and brine successively
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (EtOAc/MeOH)
  7. customby crystallized from hot EtOAc

出典と根拠

ORDレコード
ord-a668cd8036fd42ba93d3cc905545f5c3
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