Sodium Carbonate → HCID 178428380, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.100 g (0.209 mmol) 3-{[4-(cyclohexylamino)-1-(3-fluorophenyl)-2-oxo-1,3,8-triazaspiro[4.5]dec-3-en-8-yl]methyl}phenylboronic acid (7-1) in 1 mL CH3CN:H2O was added 0.030 g (0.174 mmol) 3-bromo-4-methylpyridine and 0.007 g (0.011 mmol) Tris(4,6-dimethyl-3sulfonatophenyl)phosphine and 0.001 g (0.004 mmol) palladium II acetate and 0.037 g (0.349 mmol) sodium carbonate. The reaction was heated in the microwave at 120° C. for 20 mins. Purification by preparative HPLC (5-95% CH3CN/H2O over 30 min, 0.05% added TFA, C18 PRO YMC 20×150 mm) afforded 4-(cyclohexylamino)-1-(3-fluorophenyl)-8-[3-(4-methylpyridin-3-yl)benzyl]-1,3,8-triazaspiro[4.5]dec-3-en-2-one as a white solid. NMR 1H NMR (CD3OD) δ 8.37 (d, J=5.04 Hz, 1H), 8.29 (s, 1H), 7.42 (m, 3H) 7.19 (m, 6H), 3.76 (m, 1H), 3.47 (s, 2H), 2.77 (m, 2H), 2.29 (s, 3H), 2.14 (m, 6H), 1.95 (m, 2H), 1.77 (m, 2H), 1.66 (m, 1H), 1.36 (m, 4H), 1.18 (m, 1H). High resolution mass spec (FT/ICR) calc M+H=526.2977 found 526.3012.

Provenance & Evidence