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Tributylphosphine → 1-(1,2-Dimethyl-1H-benzimidazol-6-yl)-4-((5-(trifluoromethyl)thiophen-3-yl)methoxy)pyridin-2(1H)-one

HRID 2203122
ノート
印刷プレビュー

反応式

HRID 2203122 の反応式
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([N:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]3=[O:18])[CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH3:19].[F:20][C:21]([F:30])([F:29])[C:22]1[S:26][CH:25]=[C:24]([CH2:27]O)[CH:23]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>C1COCC1>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([N:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:27][C:24]4[CH:23]=[C:22]([C:21]([F:30])([F:29])[F:20])[S:26][CH:25]=4)=[CH:13][C:12]3=[O:18])[CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH3:19]
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 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 199573935-(Trifluoromethyl)-3-thiophenemethanolHCID 896909671-(1,2-Dimethyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one

生成物 1

HCID 896913081-(1,2-Dimethyl-1H-benzimidazol-6-yl)-4-((5-(trifluoromethyl)thiophen-3-yl)methoxy)pyridin-2(1H)-one収率 78.5%

試薬・触媒・溶媒

1
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a suspension of 1-(1,2-dimethyl-1H-benzo[d]imidazol-6-yl)-4-hydroxypyridin-2(1H)-one (100 mg) in THF (5 ml) were added (5-(trifluoromethyl)thiophen-3-yl)methanol (78 mg), 1,1′-(azodicarbonyl)dipiperidine (128 mg) and tributylphosphine (0.13 ml) at room temperature, and the mixture was stirred at 50° C. overnight. After cooling, the mixture was purified by NH silica gel column chromatography (EtOAc/MeOH). The same reaction was conducted, and the combined products were purified by preparative HPLC (C18, mobile phase: H2O/CH3CN (0.1% TFA included)). The desired fraction was neutralized with saturated NaHCO3 solution, and extracted with EtOAc. The organic layer was separated, dried over MgSO4 and concentrated in vacuo to give the title compound (129 mg) as a white solid.

後処理

  1. temperatureAfter cooling
  2. customthe mixture was purified by NH silica gel column chromatography (EtOAc/MeOH)
  3. customThe same reaction
  4. customthe combined products were purified by preparative HPLC (C18, mobile phase: H2O/CH3CN (0.1% TFA included))
  5. extractionextracted with EtOAc
  6. customThe organic layer was separated
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0b2e225bac984edda1d121c22846798c
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

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