Sodium Carbonate → HCID 67216242, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[(5R,7S)-7-(4-bromo-phenyl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl]-3-fluoro-benzonitrile (25 mg, 63 μmol) in DME:H2O (4:1, 1 ml) were added Na2CO3 (10 mg, 94 μmol) and 4-methoxyphenylboronic acid (10.5 mg, 69 μmol). To this stirred mixture, PdCl2(dppf).CH2Cl2 complex (1.03 mg, 1.26 μmol) was added. The reaction was carried out under sealed-vessel microwave heating at 120° C. for 10 minutes using a Biotage Initiator™ (pre-stirring: 10 s, absorption level: very high). Upon completion, the mixture was allowed to cool to room temperature, the Pd catalyst was filtered off and the solvent was removed. The crude product obtained was purified using preparative LC-MS and lyophilized to give 3-fluoro-4-[(5R,7S)-7-hydroxy-7-(4′-methoxy-biphenyl-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl]-benzonitrile (13 mg, >95% purity). MS 426.0 (M+H), LCMS condition C, retention time 2.06 min. 1H NMR (600 MHz, DMSO-d6) δ ppm 2.90 (dd, 1H), 3.43-3.48 (m, 1H), 3.78 (s, 3H), 6.17 (dd, 1H), 6.59 (br. s., 1H), 7.01-7.03 (m, 2H), 7.33 (t, 1H), 7.53 (d, 2H), 7.60-7.62 (m, 2H), 7.63-7.65 (m, 2H), 7.78 (dd, 1H), 8.02 (dd, 1H), 8.94 (br. s., 1H).

Provenance & Evidence