(4-Amino-3'-chloro-biphenyl-3-yl)-propynyl-methanone → (4-Amino-3'-chloro-biphenyl-3-yl)-dipropynyl-methanol

Participants

Reaction Steps

Following the procedure of Example 41, (4-amino-3′-chloro-biphenyl-3-yl)-propynyl-methanone (mp 112-114° C.; MS ((+) ESI) m/z 270/272 (M+H)+) was treated with propynylmagnesium bromide to give (4-amino-3′-chloro-biphenyl-3-yl)-dipropynyl-methanol which was reacted with 1,1′-carbonyldiimidazole to afford the title compound. Yellow solid: mp 151° C. (decomposed); 1H-NMR (DMSO-d6) δ 10.8 (s, 1H), 7.71 (dd, 1H, J=8.52, 1.94 Hz), 7.69 (m, 2H), 7.61 (d, 1H, J=7.64 Hz), 7.50 (t, 1H, J=7.85 Hz), 7.43 (d, 1H, J=7.99 Hz), 7.06 (d, 1H, J=8.23 Hz), 2.0 (s, 6H); MS (APCI) m/z 336 ([M+H]+, 20%).

Provenance & Evidence