tert-Butyl methyl ether → HCID 86690648, compound

Participants

Reaction Steps

In a vial, N-[(4-bromophenyl)methyl]-N-isobutyl-1-phenyl-methanesulfonamide (53 mg, 0.13 mmol), 2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl (3.2 mg, 0.0067 mmol), chloro(2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl)[2-(2 aminoethylphenyl)]palladium(II), methyl-t-butylether adduct (6 mg, 0.0067 mmol) and sodium tert-butoxide (20 mg, 0.20 mmol) were combined and the vial was purged with nitrogen. 1,4-Dioxane (1 mL) and cyclopropyl(piperazin-1-yl)methanone (31 mg, 0.20 mmol) were then added and the reaction was stirred at ambient temperature for 16 hours. The reaction was then partitioned between water and dichloromethane and the dichloromethane layer was isolated with a phase separator cartridge, concentrated and purified by preparative reverse phase HPLC to yield 27 mg of N-[4-(4-cyclopropanecarbonyl-piperazin-1-yl)-benzyl]-N-isobutyl-C-phenyl-methanesulfonamide. 1H NMR (400 MHz, DMSO) δ 7.38-7.34 (m, 5H), 7.21 (d, J=8.5 Hz, 2H), 6.94 (d, J=6.8 Hz, 2H), 4.40 (s, 2H), 4.16 (s, 2H), 3.82-3.78 (m, 2H), 3.62-3.58 (m, 2H), 3.20-3.05 (m, 4H), 2.80 (d, J=7.5, 2H), 2.12-1.92 (m, 1H), 1.60-1.45 (m, 1H), 0.83-0.69 (m, 4H), 0.67 (d, J=7.1 Hz, 6H); LCMS (m/z) ES+ 470.2 [M+1]+.

Provenance & Evidence