Potassium Phosphate, Tribasic → N-(2-Fluoro-4-nitrophenyl)-2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-amine

Participants

Reaction Conditions

Reaction Steps

A suspension of 175 (500 mg, 2.00 mmol, scheme 35), 416 (406 mg, 2.60 mmol), Pd2(dba)3 (73 mg, 0.08 mmol), (2-biphenyl)dicyclohexylphosphine (56 mg, 0.16 mmol), and K3PO4 (638 mg, 3.00 mmol) in toluene (20 ml) was degassed for 15 min with nitrogen, and then heated at 110° C. for 22 hrs in a sealed flask [ J. P. Wolfe, H. Tomori J. P. Sadighi J. Yin, S. L. Buchwald J. Org. Chem. 2000, 65, 1158-1174]. After cooling to room temperature the reaction mixture was filtered, the filtrate was concentrated and the residue was adsorbed on silica gel and subjected to flash column chromatography (eluents MeOH/CH2Cl2: 2/98 to 10/90). Fractions containing the product were combined, concentrated and treated with AcOEt/hexanes to afford title compound 417 (370 mg, 50% yield) as a yellow-orange solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.57 (bs, 1H), 8.45 (d, J=5.1 Hz, 1H), 8.22 (dd, J=11.3, 2.5 Hz, 1H), 8.06 (dd, J=8.9, 2.3 Hz, 1H), 7.83 (d, J=1.2 Hz, 1H), 7.70 (d, J=1.2 Hz, 1H), 7.63 (s, 1H), 7.24 (t, J=8.7 Hz, 1H), 6.94 (bd, J=4.7 Hz, 1H), 3.71 (s, 3H). LCMS: 370.0 (M+H)+.

Provenance & Evidence