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

HRID 473054

반응식

HRID 473054 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.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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 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 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.

후처리

  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

출처 및 근거

ORD 기록
ord-6becbcf7f69841c2875688099706b4fb
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633239B2

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