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

HRID 473054

Reaction equation

HRID 473054 reaction equation
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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6becbcf7f69841c2875688099706b4fb
Source dataset
uspto-grants-2014_01
Patent number
US08633239B2

Linked notes

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