(6-Bromoquinazolin-4-yl)[4-(phenylmethoxy)phenyl]amine → HCID 22609706, compound

Participants

Reaction Steps

The (4-benzyloxy-phenyl)-(6-bromoquinazolin-4-yl)-amine (200 mg, 0.49 mmol), 5-(tributylstannyl)-2,3-dihydrofuran (250 mg, 0.70 mmol) and bis(triphenylphosphine)palladium(II) chloride (catalytic) were dissolved in dioxan (10 ml) and heated at reflux under nitrogen for 2 hr (Procedure B). The solvent was removed from the cooled reaction under vacuum, and the residue was suspended in 1:1 iso-hexane/ethyl acetate and filtered. The solvent was removed from the filtrate under vacuum to give the product (140 mg, 72%) as a yellow solid; δH [2H6]-DMSO 9.88 (1H, b, NH), 8.62 (1H, s, 5-H), 8.50 (1H, s, 2-H), 8.05 (1H, d, 7-H), 7.67 (3H, m, 8-H, 2′-H, 6′-H), 7.55-7.29 (5H, m, 5×Ph-H), 7.03 (2H, m, 3′-H, 5′-H), 5.81 (1H, s, 3″-H), 5.12 (2H, s, PhCH2), 4.52 (2H, t, 5″-H2), 2.88 (2H, t, 4″-H2); m/z 396 (M+1)+.

Provenance & Evidence