Sodium Carbonate → 1,1-Dimethylethyl 2-{4-[(4-hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}-1H-pyrrole-1-carboxylate

Participants

Reaction Steps

To a round-bottomed flask were added 4-[(4-bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol (14) (0.127 g, 0.32 mmoL), 1-N-BOC-pyrrole-2-boronic acid (0.21 g, 1.0 mmoL), tetrakis(triphenylphosphine)palladium(0) (0.033 g, 0.029 mmoL), 2 M Na2CO3 (3 mL), and ethylene glycol dimethyl ether (8 mL). The stirred reaction mixture was heated at reflux overnight under a nitrogen atmosphere. The oil bath was removed and the reaction mixture was allowed to cool at RT. The reaction mixture was transferred to a separatory funnel and partitioned between H2O and EtOAc. The organic phase was separated, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo to give an orange-brown oil. The crude product was purified by flash chromatography on silica gel with a hexanes:EtOAc gradient (100:0 to 80:20) to give 111 mg (72%) of compound 18 as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 0.88 (s, 12H), 1.24 (m, 11H), 1.92 (s, 2H), 1.94 (s, 2H), 6.19 (m, 1H), 6.23 (m, 1H), 6.65 (d, J=8.5 Hz, 2H), 6.92 (d, J=8.4 Hz, 2H), 7.09 (d, J=8.1 Hz, 2H), 7.21 (d, J=8.0 Hz, 2H), 7.31 (m, 1H), 9.27 (s, 1H). LCMS (ESI): m/z 508 (M+Na)+.

Provenance & Evidence