Ethyl Acetate → HCID 90404051, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example A4 (0.35 g, 1.318 mmol) in toluene (8 mL) was sparged with Ar, treated with 5-(tributylstannyl)thiazole (0.493 g, 1.318 mmol) and Pd(PPh3)4 (0.152 g, 0.132 mmol), heated at 110° C. for 16 h, then cooled to RT. The mixture was treated with EtOAc and 10% aq. KF solution, stirred for 1 h and the solids were removed via filtration through diatomaceous earth. The layers of the filtrate were separated, the aqueous layer extracted with additional EtOAc (1×) and the combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 5-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)thiazole (270 mg, 65%) as a pale orange solid. 1H NMR (400 MHz, DMSO-d6): δ 9.14 (s, 1H), 8.62 (s, 1H), 8.53 (d, J=5.7 Hz, 1H), 8.24 (d, J=8.7 Hz, 1H), 7.90 (d, J=8.7 Hz, 1H), 7.81 (d, J=2.4 Hz, 1H), 7.06 (dd, J=5.7, 2.4 Hz, 1H), 2.51 (s, 3H); MS (ESI) m/z: 315.1 (M+H+).

Provenance & Evidence