3-Nitrophenylboronic Acid → 3-Hydroxy-5-(3'-nitro-biphenyl-4-yl)-pentanoic acid

Participants

Reaction Conditions

Reaction Steps

3-Hydroxy-5-(4iodo-phenyl)-pentanoic acid (Intermediate 10, 16 mg, 50 μmol), cesium carbonate (40 mg, 125 μmol), 3-nitrophenylboronic acid (10 mg, 60 μmol) and FibreCat™ 1001 (20 mg, 2.7% w/w palladium) were suspended in dimethylformamide (200 μL) and then heated at 100° C. for 1 hour. The reaction was cooled to room temperature and the solvent removed under reduced pressure. The residue was partitioned between 10% methanol/dichloromethane and 2 M HCl then the phases separated. The organic phase was evaporated under reduced pressure and the residue purified via mass directed HPLC to give the title compound (5 mg, 32%) as a white solid. LC/MS: 3.18 min; z/e 314, calcd (M−1) 314. 1H NMR (400 MHz: DMSO-d6): 8.4 (1 H), 8.15 (2 H), 7.7 (3 H), 7.35 (2 H), 3.85 (1 H), 2.7 (2 H), 2.32 (2 H), 1.7 (2 H).

Provenance & Evidence