Benzo(B)Thiophene-2-Boronic Acid → HCID 22998519, compound

HRID 1166975Notes

Reaction equation

HRID 1166975 reaction equation
[S:1]1[C:5](B(O)O)=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.Br[C:14]1[S:18][C:17]([S:19]([N:22]2[CH:26]=[CH:25][CH:24]=[CH:23]2)(=[O:21])=[O:20])=[CH:16][CH:15]=1>>[S:1]1[C:5]([C:14]2[S:18][C:17]([S:19]([N:22]3[CH:26]=[CH:25][CH:24]=[CH:23]3)(=[O:20])=[O:21])=[CH:16][CH:15]=2)=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Participants

3

Reactant 2

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 23445587N-(5-bromothiophenesulfonyl)pyrrole

Product 1

HCID 22998519HCID 22998519, compoundYield 68%

Procedure

N-[5-(benzo[b]thien-2-yl)thiophene-2-sulfonyl]pyrrole was prepared in the same manner as described in Example 32C from benzo[b]thiophene-2-boronic acid (426 mg, 2.39 mmol) and N-(5-bromothiophene-2-sulfonyl)pyrrole (700 mg, 2.39 mmol). Purification by column chromatography using 2% ethyl acetate/hexanes gave the pure sulfonamide in 68% yield as a brownish-red solid.

Workup

  1. customPurification by column chromatography

Sources & evidence

ORD record
ord-c4842b1cf0ad487abb8b8cb21ea0b747
Source dataset
uspto-grants-2003_09
Patent number
US06613804B2

Reaction notes

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