Ethyl Acetate → HCID 57757233, compound

Participants

Reaction Steps

To a solution of 4-[(4-bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol (14) (0.1 g, 0.250 mmol) and (4-acetylaminophenyl)boronic acid (0.148, 0.826 mmol) in ethylene glycol dimethyl ether (8 mL) was added tetrakis(triphenylphosphine)palladium (0) (0.026 g, 0.023 mmol) followed by 2 M Na2CO3 (3 mL). The reaction mixture was refluxed for 4 h, cooled to room temperature then diluted with water followed by EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water followed by brine, dried (MgSO4) filtered and concentrated to an oil. The crude oil was dissolved in DCM, loaded onto silica gel and purified with a gradient of 100% hexanes to 40% hexanes:EtOAc over 60 mins. Pure fractions were combined and concentrated to give 0.05 g (41%) of the title compound 99 as an off white powder. 1H NMR (400 MHz, DMSO-d6): δ 0.89 (s, 12 H), 1.25 (s, 2 H), 1.93 (s, 4 H), 2.03 (s, 3 H), 6.66 (d, J=8.5 Hz, 2 H), 6.94 (d, J=8.4 Hz, 2 H), 7.16 (d, J=8.3 Hz, 2 H) 7.52-7.64 (m, 6 H), 9.27 (s, 1 H), 9.99 (s, 1 H). HRMS (ESI) Calcd for C31H36NO2: 454.2746 (M+H)+. Found 454.2757.

Provenance & Evidence