Sodium Carbonate → HCID 11443047, compound

Participants

Reaction Steps

The Suzuki protocol described for (163) was employed. A round bottom flash was charged with 4-[(4-bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol (14) (0.200 g, 0.5 mmol), PdCl2(PPh3)2 (0.035 g, 0.05 mmol), [4-(4-morpholinyl)phenyl]boronic acid (0.270 g, 1.0 mmol), aqueous 2 M Na2CO3 (1.0 mL, 0.106 g, 1.0 mmol) solution, and 4:1 THF:H2O mixture (5 mL) under a nitrogen atmosphere. The reaction mixture was refluxed for 3 h. Regular work-up and purification gave 0.142 g (59%) of the title compound (236) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.27 (s, 1H), 7.52 (d, J=5.2 Hz, 2H), 7.50 (d, J=4.4 Hz, 2H), 7.13 (d, J=8.4 Hz, 2H), 6.98 (d, J=8.8 Hz, 2H), 6.94 (d, J=8.4 Hz, 2H), 6.66 (d, J=8.4 Hz, 2H), 3.72 (t, J=4.4 Hz, 4H), 3.12 (t, J=4.8 Hz, 4H), 1.93 (s, 2H), 1.92 (s, 2H), 1.25 (s, 2H), 0.89 (s, 12H). LCMS (APCI): m/z 482.08 (M+H)+.

Provenance & Evidence