Sodium Carbonate → HCID 66652141, compound

Participants

Reaction Conditions

Reaction Steps

Combine trifluoro-methanesulfonic acid 8-methoxy-4-(4-methoxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalen-6-yl ester (0.046 g, 0.1 mmol), 4-chlorophenyboronic acid (0.019 g, 0.12 mmol), tetrakis(triphenylphosphine)palladium(0) (0.006 g, 5 mole %), sodium carbonate (0.12 ml 2N), and toluene/ethanol (4-1). Purge in vacuo briefly, and heat at 90° C. for 12 hours. Remove solvent, take in ethyl acetate and wash with water. Dry over anhydrous sodium sulfate and chromatograph the residue on silica gel with 5% ethyl acetate in hexanes to yield the titled compound (0.13 g, 31%). 1H NMR (CDCl3): 7.34 (d, J=8.8 Hz, 2H), 7.26 (d, J=8.8 Hz, 2 H), 7.1 (d, J=8.87 Hz, 2H), 6.8 (d, J=8.8 Hz, 2H), 6.78 (s, 1H), 6.62 (s, 1H), 3.82 (s, 3H), 3.77 (s, 3H), 3.45 (m, 1H), 2.98 (m, 1H), 2.85(m, 1H), 2.57 (m, 1H), 2.3 (m, 1H), 2.21 (m, 1H), 1.65-1.2 (m, 5H).

Provenance & Evidence