Methanol → HCID 59393680, compound

Participants

Reaction Conditions

Reaction Steps

Palladium (II) acetate (81.0 mg, 0.360 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (401 mg, 0.720 mmol) were added to a stirred solution of 4b (1.60 g, 3.62 mmol) in triethylamine:DMF:methanol (25.0 mL of a 1:10:10 mixture, respectively) at rt. The reaction mixture was saturated with carbon monoxide and then heated to 70° C. under a carbon monoxide atmosphere (balloon) for approximately 3.5 h. After cooling to rt, the reaction mixture was filtered through a short column of CELITE®, eluting with DCM. The filtrate was partially concentrated in vacuo and diluted with EtOAc. The organic phase was washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 40%-80% EtOAc/hexanes as eluent) afforded the title compound 4c. m/z (ES) 469 (MH)+. 1HNMR. (500 MHz, CDCl3): δ 9.31 (d, 1H, J=1.9 Hz), 8.45 (m, 2H), 8.29 (d, 2H, J=8.7 Hz), 8.03 (d, 1H, J=8.7 Hz), 7.50 (m, 6H), 4.12 (s, 3H), 3.94 (s, 3H), 3.22 (m, 1H), 1.81 (s, 3H), 0.93 (d, 3H, J=6.6 Hz), 0.89 (d, 3H, J=6.6 Hz).

Provenance & Evidence