Triethylamine → (E)-5-(2-(phenylsulfonyl)vinyl)-1H-indole

HRID 473054

反応式

HRID 473054 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[C:11]1([S:17]([CH:20]=[CH2:21])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.C(N(CC)CC)C>CN(C=O)C.ClCCl.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:11]1([S:17](/[CH:20]=[CH:21]/[C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 249055-BromoindoleHCID 79664Phenyl vinyl sulfoneHCID 80271Tri-o-tolylphosphine

生成物 1

HCID 15521560(E)-5-(2-(phenylsulfonyl)vinyl)-1H-indole収率 85%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 5-bromoindole (5.0 g, 25.5 mmol), phenylvinylsulfone (7.50 g, 44.64 mmol), Pd(OAc)2 (0.46 g, 2.05 mmol), tri-O-tolylphosphine (1.55 g, 5.10 mmol) and triethylamine (4.88 g, 48.46 mmol) was heated to 95-105° C. for 6-15 h in DMF. The reaction mixture was cooled to RT, diluted with dichloromethane and filtered over a bed of filter aid. The filtrate was sequentially washed with water and brine, and dried over sodium sulphate. The organic layer was concentrated under vacuum and the product precipitated from dichloromethane and hexane as a solid in about 85-90% yield.

後処理

  1. filtrationfiltered over a bed of filter aid
  2. washThe filtrate was sequentially washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. concentrationThe organic layer was concentrated under vacuum
  5. customthe product precipitated from dichloromethane and hexane as a solid in about 85-90% yield

出典と根拠

ORDレコード
ord-6becbcf7f69841c2875688099706b4fb
出典データセット
uspto-grants-2014_01
特許番号
US08633239B2

関連ノート

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