Tetrahydrofuran → HCID 68487879, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of potassium carbonate (85.4 mg 0.618 mmol), 2-methylphenylboronic acid (63.3 mg, 0.466 mmol), 1-[6-iodo-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (110 mg, 0.204 mmol), and THF (1.5 ml) was degassed for 5 minutes with nitrogen in a sealable tube. The dichloromethane adduct of 1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium (20.2 mg, 0.0246 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 (10 ml), and filtered. The filtrate was concentrated. The residue was purified by FCC (3-40% EtOAc/hexanes) to yield the titled compound (92.0 mg, 90%). MS (ESI): mass calcd. for C27H32N4O4Si, 504.22; m/z found, 446.6 [M−CH2OCH2CH2+H]+. 1H NMR (600 MHz, CDCl3): 8.68 (d, J=0.6 Hz, 1H), 8.31-8.30 (m, 1H), 8.18 (d, J=0.6 Hz, 1H), 7.79 (dd, J=8.3, 2.1 Hz, 1H), 7.76-7.74 (m, 1H), 7.33-7.28 (m, 4H), 5.91 (s, 2H), 4.39-4.35 (m, 2H), 4.37 (q, J=7.2 Hz, 2H), 2.31 (s, 3H), 1.39 (t, J=7.1 Hz, 3H), 0.83-0.79 (m, 2H), −0.08 (s, 9H).

Provenance & Evidence