4-Bromobenzenesulfonamide → 2-Phenylbenzene-1-sulfonamide

HRID 133402

Reaction equation

HRID 133402 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1>[Pd]>[C:6]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=[CH:2][CH:7]=1

Participants

3

Reactant 1

HCID 696964-Bromobenzenesulfonamide

Product 1

HCID 123715202-Phenylbenzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In Scheme 1 the compounds of the invention, 1, are prepared in 4 steps. Sulfonylation of valine methyl ester with 4-bromo-benzenesulfonyl chloride was carried out in the presence of Hunig base to give sulfonamide Intermediate 1. This 4-bromo-benzenesulfonamide was furthered coupled with boronate ester using Palladium catalyst under Suzuki coupling condition to provide biphenyl sulfonamide Intermediate 2. Biphenyl sulfonamide Intermediate 2 was then alkylated with various alkylating reagents to provide biphenyl sulfonamide ester (Intermediate 3). Hydrolysis of Intermediate 3 was carried out using bases such as NaOH, or LiOH to form the final product 1.

Sources & evidence

ORD record
ord-68ca173bd40c4077ab21cedd0d8e35de
Source dataset
uspto-grants-2008_06
Patent number
US07390833B2

Linked notes

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