Sodium Bicarbonate → Quinazoline

Participants

Reaction Steps

0.20 g of 6-iodo-4-(7-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)quinazoline, 0.28 g of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine, 0.11 g of sodium hydrogencarbonate and 0.03 g of Pd(PPh3)2Cl2 in 5.00 ml of dioxane and 0.50 ml of water are heated at 90° C. under nitrogen in a flask until the reaction is complete (HPLC check, about 5 hours). The cooled reaction solution is diluted with EA and washed 3 times with water. The organic phase is dried over sodium sulfate and purified by means of column chromatography (gradient EA: methanol 5-30% in 13 min), giving 0.20 g of 4-(7-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)-6-[2-methyl-3-[(2-trimethylsilanylethoxymethyl)-3H-imidazo]4,5-b]pyridin-6-yl]quinazoline as white powder (yield 64%, content 79%); MS-FAB (M+H+)=553.3; Rf (polar method): 2.14 min.

Provenance & Evidence