Tolylboronic acid → HCID 15453182, compound

HRID 378437Notes

Reaction equation

HRID 378437 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][S:8]([C:11]2[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[O:4][N:3]=1.[CH3:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>O>[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][S:8]([C:11]2[CH:16]=[CH:15][C:14]([C:22]3[CH:23]=[CH:24][C:19]([CH3:18])=[CH:20][CH:21]=3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 79799Tolylboronic acidHCID 15453181N-(3-methyl-5-isoxazolyl)-4-bromobenzenesulfonamide

Product 1

HCID 15453182HCID 15453182, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Nitrogen was bubbled through a biphasic mixture of ethanol (15 ml), toluene (15 ml) and 2M sodium carbonate solution (15 ml). N-(3-methyl-5-isoxazolyl)-4-bromobenzene sulfonamide (0.951 g, 3 mmol), 4-methylbenzeneboronic acid (0.56 g, 4 mmol) and tetrakistriphenylphosphine palladium (0) (300 mg) were added. The reaction mixture was kept at 80° C., under a N2 atmosphere for 24 h, with stirring, and was then diluted with water (50 ml) and extracted with ether (50 ml) to remove neutral impurities and excess 4-methylbenzeneboronic acid. The aqueous phase was neutralized to pH 2 using concentrated hydrochloric acid and the resultant solid was filtered. This was dried under vacuum and recrystallized using hexane/ethyl acetate giving N-(3-methyl-5-isoxazolyl)-4-(4-methylphenyl)benzenesulfonamide (1.0 g, 100% yield, m.p. 194-198° C.).

Workup

  1. customNitrogen was bubbled through a biphasic mixture of ethanol (15 ml), toluene (15 ml) and 2M sodium carbonate solution (15 ml)
  2. extractionextracted with ether (50 ml)
  3. customto remove neutral impurities and excess 4-methylbenzeneboronic acid
  4. filtrationthe resultant solid was filtered
  5. customThis was dried under vacuum
  6. customrecrystallized

Sources & evidence

ORD record
ord-ebc81deac0a44bf68be8b35b1883e964
Source dataset
uspto-grants-2000_02
Patent number
US06030991

Reaction notes

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