(4-Benzyloxy-phenyl)-(6-iodoquinazolin-4-yl)-amine → (4-Benzyloxy-phenyl)-(6-[5-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)furan-2-yl]quinazolinyl)-amine

Participants

Reaction Steps

(4-Benzyloxy-phenyl)-(6-iodoquinazolin-4-yl)-amine (0.925 g, 2.04 mmol), 5-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-2-[tri(n-butyl)stannyl]furan (2.00 g, 4.1 mmol) and bis(triphenylphosphine)palladium (II) chloride (catalytic) were reacted in dry dioxane (25 ml) according to Procedure B. Purification by silica gel chromatography and eluting with 100% EtOAc gave the title compound as a yellow solid (0.700 g, 1.34 mmol, 66%); δH [2H6]DMSO 10.0 (1H, s), 8.75 (1H, s), 8.48 (1H, s), 8.12 (1H, d), 7.79 (1H, d), 7.66 (2H, d), 7.30-7.52 (5H, m), 7.03-7.12 (3H, m), 6.64 (1H, d), 5.14 (2H, s), 4.06 (6H, s), 0.85 (3H, s).

Provenance & Evidence