Sodium hydride → 4-[(1-Ethylpyrrolidin-3-yl)oxy]phenyl 2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl Ketone

HRID 377410ノート

反応式

HRID 377410 の反応式
[H-].[Na+].[CH2:3]([N:5]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6]1)[CH3:4].[N:11]1([CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[S:29][C:28]4[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=4[C:26]=3[C:34]([C:36]3[CH:41]=[CH:40][C:39](F)=[CH:38][CH:37]=3)=[O:35])=[CH:21][CH:20]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1>CN(C=O)C.[Cl-].[Na+].O>[N:11]1([CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[S:29][C:28]4[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=4[C:26]=3[C:34]([C:36]3[CH:41]=[CH:40][C:39]([O:10][CH:7]4[CH2:8][CH2:9][N:5]([CH2:3][CH3:4])[CH2:6]4)=[CH:38][CH:37]=3)=[O:35])=[CH:23][CH:24]=2)[CH2:12][CH2:13][CH2:14][CH2:15]1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 982031-Ethyl-3-pyrrolidinolHCID 107182054-Fluorophenyl 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl ketone

生成物 1

HCID 211828674-[(1-Ethylpyrrolidin-3-yl)oxy]phenyl 2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl Ketone収率 63%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

Sodium hydride (60% oil dispersion, 38 mg) was suspended in DMF (1 mL) and stirred at ambient temperature for 15 min under argon before 1-ethyl-3-pyrrolidinol (92 μL) was added. After stirring for 15 min, 4-fluorophenyl 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl ketone (223 mg) in 1 mL of DMF was introduced and the resulting solution was stirred at ambient temperature for 4 h. The reaction mixture was diluted with brine (50 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Chromatography with Et3N:MeOH:EtOAc (5:5:90) afforded the product as a colorless oil (171 mg, 63%).

後処理

  1. additionwas added
  2. stirringthe resulting solution was stirred at ambient temperature for 4 h
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-499bfbf9b64e471282807f29e1d3da22
出典データセット
uspto-grants-2000_02
特許番号
US06025382

反応ノート

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