4-(Trifluoromethyl)phenylboronic acid → N-{5-[4-(trifluoromethyl)phenyl]thiophene-2-sulfonyl}pyrrole

HRID 1166962

Reaction equation

HRID 1166962 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:15]1[S:19][C:18]([S:20]([N:23]2[CH:27]=[CH:26][CH:25]=[CH:24]2)(=[O:22])=[O:21])=[CH:17][CH:16]=1>>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([C:15]2[S:19][C:18]([S:20]([N:23]3[CH:27]=[CH:26][CH:25]=[CH:24]3)(=[O:21])=[O:22])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 23445587N-(5-bromothiophenesulfonyl)pyrrole

Product 1

HCID 22998451N-{5-[4-(trifluoromethyl)phenyl]thiophene-2-sulfonyl}pyrroleYield 75%

Procedure

N-{5-[4-(trifluoromethyl)phenyl]thiophene-2-sulfonyl}pyrrole was prepared in the same manner as described in Example 32C using 4-trifluoromethylbenzene boronic acid and N-(5-bromothiophene sulfonyl)pyrrole. Purification by column chromatography using 2% ethyl acetate/hexanes gave the pure sulfonamide as a white powder in 75% yield.

Workup

  1. customPurification by column chromatography

Sources & evidence

ORD record
ord-af24c1913aad43beb8e8e3ca1c23881f
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Linked notes

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