Tetrahydrofuran → HCID 68488561, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of potassium carbonate (210 mg 1.52 mmol), phenylboronic acid (156 mg, 1.28 mmol), 1-[7-iodo-3-(2-methoxy-ethoxymethyl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (250 mg, 0.502 mmol), and THF (4.4 ml) was degassed with nitrogen for 10 min in a sealable tube. The dichloromethane adduct of 1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium (48.9 mg, 0.0610 mmol) was added to the reaction mixture and the pressure tube was sealed. The reaction mixture was stirred at 80° C. for 18 h. The reaction mixture was cooled to 23° C., diluted with DCM (15 mL), and filtered. The filtrate was concentrated. The residue was purified by FCC (5-45% EtOAc/hexanes) to yield the titled compound (192 mg, 85%). MS (ESI): mass calcd. for C24H24N4O5, 448.2; m/z found, 449.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 8.88 (d, J=0.6 Hz, 1H), 8.30 (d, J=0.6 Hz, 1H), 8.04 (d, J=1.5 Hz, 1H), 8.00 (dd, J=8.3, 1.8 Hz, 1H), 7.88-7.84 (m, 2H), 7.78 (dd, J=8.0, 1.5 Hz, 1H), 7.58-7.52 (m, 2H), 7.51-7.46 (m, 1H), 5.67 (s, 2H), 4.30 (q, J=7.1 Hz, 2H), 3.54-3.50 (m, 2H), 3.29-3.25 (m, 2H), 3.08 (s, 3H), 1.32 (t, J=7.1 Hz, 3H).

Provenance & Evidence