Tributylphosphine → 4-((4-Chlorothiophen-2-yl)methoxy)-1-(2-ethyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2203063ノート

反応式

HRID 2203063 の反応式
[CH2:1]([C:3]1[N:7]([CH3:8])[C:6]2[CH:9]=[C:10]([N:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]3=[O:20])[CH:11]=[CH:12][C:5]=2[N:4]=1)[CH3:2].[Cl:21][C:22]1[CH:23]=[C:24]([CH2:27]O)[S:25][CH:26]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[Cl:21][C:22]1[CH:23]=[C:24]([CH2:27][O:19][C:16]2[CH:17]=[CH:18][N:13]([C:10]3[CH:11]=[CH:12][C:5]4[N:4]=[C:3]([CH2:1][CH3:2])[N:7]([CH3:8])[C:6]=4[CH:9]=3)[C:14](=[O:20])[CH:15]=2)[S:25][CH:26]=1

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 67154484(4-Chlorothiophen-2-yl)methanolHCID 896909981-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one

生成物 1

HCID 896912044-((4-Chlorothiophen-2-yl)methoxy)-1-(2-ethyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a solution of 1-(2-ethyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one (150 mg), (4-chloro-thiophen-2-yl)methanol (167 mg) and tributylphosphine (338 mg) in THF (15 ml) was added 1,1′-(azodicarbonyl)dipiperidine (422 mg), and the mixture was stirred under at 60° C. for 4 h. The reaction mixture was then cooled to room temperature, and concentrated in vacuo. The residue was diluted with DCM, washed with water and brine successively, dried over Na2SO4, concentrated in vacuo, and purified by silica gel column chromatography (MeOH/DCM) to afford the title compound as a white solid.

後処理

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with DCM
  4. washwashed with water and brine successively
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel column chromatography (MeOH/DCM)

出典と根拠

ORDレコード
ord-14ae17a8f0024f79b8e46c37a5be6792
出典データセット
uspto-grants-2016_06
特許番号
US09365540B2

反応ノート

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