Acetate → Methyl 6-{1-hydroxy-1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}pyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

The product of Step 1 (500 mg, 0.932 mmol), palladium (TT) acetate (20.93 mg, 0.093 mmol), and 1,3-bis(diphenylphosphino)propane (38.4 mg, 0.093 mmol) were combined in a 5 ml microwave vial, sealed, and taken up in DMF (4 ml)/MeOH (2.000 ml). CO was bubbled through the reaction mixture for 5 min. Triethylamine (0.260 ml, 1.864 mmol) was added, a CO balloon was attached, and the reaction was stirred at 70° C. for 2 days. The reaction was diluted with aqueous saturated NH4Cl and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated. Chromatography on silica gel (Biotage 100 g SNAP, 0-50% EtOAc/hexanes) provided methyl 6-{1-hydroxy-1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}pyridine-3-carboxylate (392 mg, 0.760 mmol, 82% yield) as a pale yellow foam. MS ESI: [M+H]+ m/z 516.1.

Provenance & Evidence