1-Isopropylpiperazine → HCID 68876458, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [5-bromo-2-(4-methylsulfanyl-phenoxy)-benzyl]-methyl-carbamic acid tert-butyl ester (300 mg, 0.684 mmol) {prepared in an analogous fashion to Example 1, Steps A-C}, isopropyl piperazine (132 mg, 1.02 mmol), XPHOS (39 mg, 0.082 mmol), Pd2(dba)3 (62.6 mg, 0.0684 mmol), and t-BuONa (98.0 mg, 1.02 mmol) in toluene was heated in a sealed tube overnight at 120° C. After cooling to rt, the mixture was filtered through diatomaceous earth and the filtrate was concentrated. Purification by FCC gave the desired product (180 mg, 54%). MS (ESI): mass calcd. for C27H39N3O3S, 485.27; m/z found, 486.4 [M+H]+. 1H NMR (CDCl3): 7.22 (d, J=8.5, 2H), 6.86-6.83 (m, 1H), 6.83-6.80 (m, 4H), 4.42-4.35 (m, 2H), 3.19-3.16 (m, 4H), 2.87-2.83 (m, 2H), 2.80-2.75 (m, 1H), 2.75-2.71 (m, 1H), 2.71-2.67 (m, 4H), 2.44 (s, 3H), 1.48-1.40 (m, 9H), 1.10 (d, J=6.5, 6H).

Provenance & Evidence