Benzene → HCID 78324475, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-(4-bromobenzyloxy)acetate (304 mg, 1.113 mmol), (R)-4-(2-(2-methylpyrrolidin-1-yl)ethyl)phenylboronic acid hydrochloride (300 mg, 1.113 mmol), tetrakis(triphenylphosphine)palladium(0) (64.3 mg, 0.056 mmol) and 2M Na2CO3 (aq.) (1113 μL, 2.226 mmol) were added to a vial with benzene (2 mL) and EtOH (0.6 mL). The reaction was heated under microwave irradiation at 100° C. for an hour and 120° C. for 0.5 h. The reaction was diluted with H2O (1 mL) and extracted with EtOAc (3×2 mL). The combined organics were filtered through a plug of MgSO4. The solvent was evaporated and the residue was purified by column chromatography and prep LCMS to give the title compound. LCMS m/z=382.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.18-1.26 (m, 3H), 1.39 (d, J=6.4 Hz, 3H), 1.54-1.70 (m, 1H), 1.85-2.12 (m, 2H), 2.15-2.29 (m, 1H), 2.96-3.14 (m, 2H), 3.14-3.28 (m, 2H), 3.40-3.49 (m, 1H), 3.54 (d, J=20.3 Hz, 1H), 3.59-3.70 (m, 1H), 4.09-4.21 (m, 4H), 4.59 (s, 2H), 7.36-7.49 (m, 4H), 7.66 (d, J=7.71 Hz, 4H), 9.51-10.13 (m, 1H).

Provenance & Evidence