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

HRID 473055

반응식

HRID 473055 반응식
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

참가 물질

8

반응물 4

HCID 249055-BromoindoleHCID 79664Phenyl vinyl sulfoneHCID 80271Tri-o-tolylphosphineHCID 81531Diisopropylethylamine

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9381a37328dc44ff90162a3771f26bff
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633239B2

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