Diisopropylamine → 4-(cyclohexylamino)-8-[[3-(2-ethenylphenyl)phenyl]methyl]-1-(3-fluorophenyl)-1,3,8-triazaspiro[4.5]dec-3-en-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.020 g (0.039 mmol) 8-(3-bromobenzyl)-4-(cyclohexylamino)-1-(3-fluorophenyl)-1,3,8-triazaspiro[4.5]dec-3-en-2-one (5-3) in 0.5 mL degassed DMF:H2O (4:1) was added 0.006 g (0.039 mmol) (2-vinylphenyl) boronic acid and 0.003 g (0.006 mmol) 3,3′,3″-Phosphinidynetris (benzene sulfonic acid) and 0.001 g (0.002 mmol) palladium II acetate and 16 μL (0.117 mmol) diisopropylamine. The reaction was heated in the microwave at 100° C. for 10 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-[(2′-vinyl-1,1′-biphenyl-3-yl)methyl]-1,3,8-triazaspiro[4.5]dec-3-en-2-one as a white solid. NMR 1H NMR (CD3OD) δ 7.65 (dd, J=6.8 Hz, 2.2 Hz, 1H), 7.43 (dt, J=7.96 Hz, 6.32 Hz, 1H), 7.34 (m, 3H) 7.17 (m, 7H), 6.61 (dd, J=17.49 Hz, 10.99 Hz, 1H), 5.70 (d, J=17.58, 1H), 5.15 (d, J=10.99 Hz, 1H), 3.75 (m, 1H), 3.46 (s, 1H), 2.78 (m, 2H), 2.14 (m, 6H), 1.93 (m, 2H), 1.74 (m, 2H), 1.63 (m, 1H), 1.34 (m, 4H), 1.17 (m, 1H). High resolution mass spec (FT/ICR) calc M+H=537.3024 found 537.3038.

Provenance & Evidence