Ethanol → tert-butyl N-[4-[3-(2-chloro-6-methyl-4-nitrophenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Participants

Reaction Conditions

Reaction Steps

2-Bromo-1-chloro-3-methyl-5-nitro-benzene (45 mg, 0.219 mmol), {[4-(3-Boranyl-dihydroxy-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (50 mg, 0.11 mmol, Example 140: step a) and Pd(PPh3)4 (25 mg, 0.02 mmol) were combined in aqueous Na2CO3 (2M, 500 μL), ethanol (500 μL) and toluene (1 mL). The reaction was heated to 80° C. overnight. The resulting residue was dissolved into EtOAc and washed with brine. The organic layers were dried (MgSO4) and the solvent was removed in vacuo followed by preparative TLC purification (30% EtOAc/hexanes) that yielded the title compound (20 mg, 29%). ESI-MS (m/z): Calcd. for C24H24CIN3O6S3: 582.1 (M+1); found: 582.1.

Provenance & Evidence