3-Aminophenylboronic acid → N-(3-methyl-5-isoxazolyl)-5-(3-aminophenyl)thiophene-2-sulfonamide

HRID 1251797Notes

Reaction equation

HRID 1251797 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.[CH3:11][C:12]1[CH:16]=[C:15]([NH:17][S:18]([C:21]2[S:22][C:23](Br)=[CH:24][CH:25]=2)(=[O:20])=[O:19])[O:14][N:13]=1>>[CH3:11][C:12]1[CH:16]=[C:15]([NH:17][S:18]([C:21]2[S:22][C:23]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([NH2:1])[CH:3]=3)=[CH:24][CH:25]=2)(=[O:20])=[O:19])[O:14][N:13]=1

Participants

3

Reactant 2

HCID 922693-Aminophenylboronic acidHCID 22998516N-(3-methyl-5-isoxazolyl)-5-bromothiophene-2-sulfonamide

Product 1

HCID 22998520N-(3-methyl-5-isoxazolyl)-5-(3-aminophenyl)thiophene-2-sulfonamide

Procedure

N-(3-methyl-5-isoxazolyl)-5-(3-aminophenyl)thiophene-2-sulfonamide was prepared in the same manner as described in Example 32C from 3-amino benzene boronic acid (256 mg, 1.87 mmol) and N-(3-methyl-5-isoxazolyl)-5-bromothiophene-2-sulfonamide (55 mg, 1.7 mmol). Purification by column chromatography using 15% MeOH/CHCl3 gave 318 mg (56%) of the product.

Workup

  1. customPurification by column chromatography

Sources & evidence

ORD record
ord-8ea63ec9646647cb8a5899c98d05c741
Source dataset
uspto-grants-2002_01
Patent number
US06342610B2

Reaction notes

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