(6-Bromoquinazolin-4-yl)[4-(phenylmethoxy)phenyl]amine → (4-Benzyloxy-phenyl)-(6-furan-2-yl-quinazolin-4-yl)-amine

Participants

Reaction Steps

The (4-benzyloxy-phenyl)-(6-bromo-quinazolin-4-yl)-amine (300 mg, 0.74 mmol), 2-(tributylstannyl)furan (290 mg, 0.81 mmol) and bis(triphenylphosphine) palladium(II) chloride (catalytic) were dissolved in dioxane (3.5 ml) and heated at reflux under nitrogen for 2 hr. The cooled reaction mixture was absorbed onto silica and purified by flash column chromatography (silica gel, eluting with 1:1 ethyl acetate/iso-hexane) to give the title product (290 mg, 79%) as a pale yellow solid; δH [2H6]-DMSO 9.94 (1H, b, NH), 8.85 (1H, s, 5-H), 8.53 (1H, s, 2-H), 8.21 (1H, d, 7-H), 7.91 (1H, d, furan-H), 7.81 (1H, d, 8-H), 7.72 (2H, d, 2′-H, 6′-H), 7.57-7.33 (5H, m, 5×Ph-H), 7.16 (1H, d, furan-H), 7.10 (2H, d, 3′-H, 5′-H), 6.72, (1H, dd, furan-4H), 5.17 (2H, s, CH2); m/z 394 (M+1)+.

Provenance & Evidence