3-Nitrophenylboronic Acid → N-(3-methyl-5-isoxazolyl)-5-(3-nitrophenyl)thiophene-2-sulfonamide

HRID 1738555Notes

Reaction equation

HRID 1738555 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:13][C:14]1[CH:18]=[C:17]([NH:19][S:20]([C:23]2[S:24][C:25](Br)=[CH:26][CH:27]=2)(=[O:22])=[O:21])[O:16][N:15]=1>>[CH3:13][C:14]1[CH:18]=[C:17]([NH:19][S:20]([C:23]2[S:24][C:25]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[CH:26][CH:27]=2)(=[O:22])=[O:21])[O:16][N:15]=1

Participants

3

Reactant 2

HCID 16773-Nitrophenylboronic AcidHCID 22998516N-(3-methyl-5-isoxazolyl)-5-bromothiophene-2-sulfonamide

Product 1

HCID 22998512N-(3-methyl-5-isoxazolyl)-5-(3-nitrophenyl)thiophene-2-sulfonamideYield 21%

Procedure

N-(3-methyl-5-isoxazolyl)-5-(3-nitrophenyl)thiophene-2-sulfonamide was prepared in the same manner as described in Example 32C from 3-nitrobenzene boronic acid (362 mg, 2.17 mmol) and N-(3-methyl-5-isoxazolyl)-5-bromothiophene-2-sulfonamide (700 mg, 2.17 mmol). Purification by column chromatography using 10% MeOH/CHCl3 gave 166 mg of the pure sulfonamide (21% yield).

Workup

  1. customN-(3-methyl-5-isoxazolyl)-5-(3-nitrophenyl)thiophene-2-sulfonamide was prepared in the same manner
  2. customPurification by column chromatography

Sources & evidence

ORD record
ord-339be60e6adc4aacabe5e8b5e8c982a5
Source dataset
uspto-grants-1999_10
Patent number
US05962490

Reaction notes

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