Iodide Ion → 4-(1,3-dihydroisoindol-2-yl)-6-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)quinazoline

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Reaction Steps

0.25 g of 4-(1,3-dihydroisoindol-2-yl)-6-iodoquinazoline, 0.32 g of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]-pyridine, 0.16 g of sodium hydrogencarbonate and 0.09 g of PdCl2(PPh3)2 in 5.00 ml of dioxane and 0.50 ml of water are heated at 90° C. under nitrogen in a flask until the iodide has reacted completely (HPLC check, about 8 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 heptane: EA 5-100% in 30 min), giving 0.12 g of 4-(1,3-dihydroisoindol-2-yl)-6-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)quinazoline as slightly beige solid (yield 33%, content 95%); MS-FAB (M+H+)=520.0; Rf (polar method): 2.77 min.

Provenance & Evidence