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

HRID 473055

反応式

HRID 473055 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.CCN(C(C)C)C(C)C>C(#N)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 249055-BromoindoleHCID 79664Phenyl vinyl sulfoneHCID 80271Tri-o-tolylphosphineHCID 81531Diisopropylethylamine

生成物 1

HCID 15521560(E)-5-(2-(phenylsulfonyl)vinyl)-1H-indole収率 65%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile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 DIPEA (3.6 g) was heated to reflux for 18 h in acetonitrile. The reaction mixture was cooled to RT, diluted with dichloromethane and filtered over a bed of filter aid. The solvent is completely distilled off and to the crude fresh dichloromethane was charged. 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 ethylacetate and hexane as a solid in about 65-70% yield.

後処理

  1. filtrationfiltered over a bed of filter aid
  2. distillationThe solvent is completely distilled off and to the crude fresh dichloromethane
  3. additionwas charged
  4. washThe filtrate was sequentially washed with water and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationThe organic layer was concentrated under vacuum
  7. customthe product precipitated from ethylacetate and hexane as a solid in about 65-70% yield

出典と根拠

ORDレコード
ord-9381a37328dc44ff90162a3771f26bff
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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