Dichloromethane → HCID 71293778, compound

Participants

Reaction Conditions

Reaction Steps

To a conical microwave vial was added pyridin-3-ylboronic acid (16 mg, 0.13 mmol), sodium carbonate (18 mg, 0.17 mmol), Pd.dppf.CH2Cl2 (7.0 mg, 0.009 mmol) followed by the addition of a solution of 3-((5R,7S)-5-(4-cyano-2-fluorophenyl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)phenyl trifluoromethanesulfonate (20 mg, 0.043 mmol) in DME (2 mL). To this crude was added 0.5 ml distilled water. The reaction was carried out under sealed-vessel microwave heating at 120° C. for 10 min using a Biotage Initiator™ (pre-stirring: 60 s, absorption level: very high). Upon completion of the reaction, the mixture was allowed to cool to room temperature, the Pd catalyst was filtered off with a plug of silica using a monster pipet. The solvent was removed. The crude was concentrated and then purified via HPLC, using 10-90% MeCN/H2O to give 8.2 mg of the entitled product. MS 397.1 (M+H); LCMS condition A, retention time 0.92 min. 1H NMR (400 MHz, CDCl3) δ ppm 2.99 (d, 1H), 3.35 (dd, 1H), 5.77 (d, 1H), 6.83 (s, 1H), 7.10-7.22 (m, 1H), 7.23-7.50 (m, 7H), 7.72-7.84 (m, 2H), 8.36-8.49 (m, 1H), 8.59 (s, 1H).

Provenance & Evidence