Triethylamine → 1-{1-[6-Chloro-1-(3,5-difluoro-benzyl)-1H-indole-3-carbonyl]-piperidin-4-yl}-1,3-dihydro-indol-2-one

HRID 1097838ノート

反応式

HRID 1097838 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]([OH:22])=O)=[CH:7][N:8]2[CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=2)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH:29]1[CH2:34][CH2:33][CH:32]([N:35]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH2:37][C:36]2=[O:44])[CH2:31][CH2:30]1.C(N(CC)CC)C>CN(C=O)C.ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]([N:29]3[CH2:34][CH2:33][CH:32]([N:35]4[C:43]5[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=5)[CH2:37][C:36]4=[O:44])[CH2:31][CH2:30]3)=[O:22])=[CH:7][N:8]2[CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=2)=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27611521-Piperidin-4-yl-1,3-dihydro-2H-indol-2-oneHCID 597567046-Chloro-1-(3,5-difluoro-benzyl)-1H-indole-3-carboxylic acid

生成物 1

HCID 249876561-{1-[6-Chloro-1-(3,5-difluoro-benzyl)-1H-indole-3-carbonyl]-piperidin-4-yl}-1,3-dihydro-indol-2-one収率 48.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of 0.10 g (0.31 mmol) 6-chloro-1-(3,5-difluoro-benzyl)-1H-indole-3-carboxylic acid and one drop of DMF in 2 ml dichloromethane were added dropwise at 0° C. 0.032 ml (0.37 mmol) oxalyl chloride. The mixture was allowed to warm to room temperature, stirred for 1 h and subsequently added dropwise to a solution of 74 mg (0.34 mmol) 1-piperidin-4-yl-1,3-dihydro-indol-2-one and 63 mg (0.62 mmol) triethylamine in 1 ml dichloromethane at room temperature. After stirring over night the reaction mixture was concentrated and the residue was purified by flash chromatography to give 78 mg (48%) of the title compound as a light yellow solid.

後処理

  1. additionwere added dropwise at 0° C
  2. stirringAfter stirring over night the reaction mixture
  3. concentrationwas concentrated
  4. customthe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-455b4d338d37435a8cbcdc0837e5a105
出典データセット
uspto-grants-2012_03
特許番号
US08143281B2

反応ノート

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