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methyl 5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinatetrifluoroacetate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
EXAMPLE 269: methyl 5-(6-(trifluoromethyl)-lH-indazol-4-yl)picolinate [0830] A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-lH-indazole (0.732 g, 2.76 mmol), (6-(methoxycarbonyl)pyridin-3-yl)boronic acid (0.5 g, 2.76 mmol) and PdCl2(dppf) (0.101 g, 0.138 mmol) in dioxane (10 mL) and aqueous saturated NaHC03 (3 mL). The resulting light brown suspension was heated at 140°C for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated. The residue was diluted with DCM, washed with water, and the volatiles removed via rotary evaporation. The crude product was purified by CombiFlash® chromatography (0-30percent MeOH in DCM over 180 minutes). The product-containing fractions were combined and concentrated by rotary evaporation to give product with some impurities (0.28 g). A portion of the product (20 mg) was re-purified by preparative HPLC, eluting with 40percent ACN (containing 0.035percent TFA) in H20 (containing 0.05percent TFA) over a period of 6.5 minutes to give a TFA salt of the title compound. 1H NMR (400 MHz, OMSO-d6) delta ppm 3.95 (s, 3 H), 7.69 (s, 1 H), 8.07 (s, 1 H), 8.23 (dd, J=8.21, 0.63 Hz, 1 H), 8.39-8.57 (m, 2 H), 9.10-9.26 (m, 1 H), 13.86 (br s, 1 H); ESI-MS m/z [M+H]+ calc'd for Ci5Hi0F3N3O2, 322.1; found 322.11.