2-Formyl-4-(tributylstannyl)thiazole → 4-(4-(4-Phenoxyphenylamino)-quinolin-7-yl) thiazole-2-carbaldehyde

Participants

Reaction Steps

Prepared according to Procedure B from (4-phenoxyphenyl)-(7-iodoquinolin-4-yl)amine (2 g, 4.56 mmol), 4-(tributylstannyl)thiazole-2-carbaldehyde (1.84 g, 4.56 mmol) and dichlorobis(triphenylphosphine)palladium (II) (0.74 g, 20 mol %) heated at reflux overnight (18 hrs) in dioxane (50 ml). The cooled solution was filtered through a plug of Celite®, concentrated and triturated with iso-hexane (3×20 ml). The resultant solid was purified via flash column chromatography on silica gel, eluting with 5% methanol in chloroform. The purified product was isolated as a yellow solid (0.85 g, 44%). δH [2H6] DMSO 10.10(1H,s), 9.30(1,bs), 8.90(1Hs), 8.50(2H,s&d), 8.45(1H,d), 8.20(1H,d), 7.40(5H,bm), 7.10(4H,2d), 6.80(1H,d).

Provenance & Evidence