Hydrochloric Acid → 5-(Pyrrolidine-1-sulfonyl)-1,3-dihydro-indol-2-one

HRID 1790966ノート

反応式

HRID 1790966 の反応式
Cl[S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)(=[O:4])=[O:3].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.N1C=CC=CC=1.Cl>ClCCl.C(OCC)(=O)C>[N:15]1([S:2]([C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8]3)(=[O:4])=[O:3])[CH2:19][CH2:18][CH2:17][CH2:16]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31268PyrrolidineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

生成物 1

HCID 220421535-(Pyrrolidine-1-sulfonyl)-1,3-dihydro-indol-2-one収率 27%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A suspension of 5-chlorosulfonyl-2-oxindole (1.62 g, 7 mmol), pyrrolidine (0.701 mL, 8.4 mmol) and pyridine (1 mL) in dichloromethane (20 mL) was stirred at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate (300 mL) and made acidic with 1 N hydrochloric acid (16 mL). The organic layer was then washed with sodium bicarbonate and brine, dried and concentrated. The residue was washed with ethanol (3 mL). It was then purified by chromatography on silica gel eluting with methanol:dichloromethane 1:9 to give 0.432 g (27%) 5-(pyrrolidine-1-sulfonyl)-1,3-dihydro-indol-2-one.

後処理

  1. washThe organic layer was then washed with sodium bicarbonate and brine
  2. customdried
  3. concentrationconcentrated
  4. washThe residue was washed with ethanol (3 mL)
  5. customIt was then purified by chromatography on silica gel eluting with methanol:dichloromethane 1:9

出典と根拠

ORDレコード
ord-ba78f745c98646a2bec87c6fbb926902
出典データセット
uspto-grants-2006_07
特許番号
US07071332B2

反応ノート

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