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With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 25℃; for 12h;
178.3 Step 3: 5-Bromo-N-(3-(2-methoxypyridin-4-yl)-1H-indazol-5-yl)-3- (trifluoromethyl)picolinamide
To a solution of 5-bromo-3-(trifluoromethyl)picolinic acid (260 mg, 962.95 umol) in pyridine (10 mL) was added EDCI (276.90 mg, 1.44 mmol) and (2-methoxypyridin-4- yl)boronic acid (347.04 mg, 1.44 mmol) and the mixture was stirred at 25 °C for 12 hrs. The mixture was concentrated and purified by flash silica gel chromatography (ISCO; 4 g SepaFlash column) using a 0-20% EtOAc/petroleum ether gradient eluent to afford the title compound (270 mg, 57%) as a yellow solid which was used without further purification. MS- ESI (m/z) calcd for C20H14BrF3N5O2 [M+H]+: 492.0/494.0. Found 492.0/494.0.
With water; sodium hydroxide In tetrahydrofuran at 25℃; for 2h;
178.2 Step 2: 5-Bromo-3-(trifluoromethyl)picolinic acid
To a solution of methyl 5-bromo-3-(trifluoromethyl)picolinate (200 mg, 699.19 umol) in THF (8 mL) and H2O (4 mL) was added NaOH (55.94 mg, 1.40 mmol) and the mixture was stirred at 25 °C for 2 hrs. The reaction mixture was diluted with 1M HCl to pH = 4. The aqueous layers were extracted with EtOAc (15 mL × 3). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to afford the title compound (187 mg) as a white solid which was used without purification. MS-ESI (m/z) calcd for C7H4BrF3NO2 [M+H]+: 269.9/271.9. Found 269.9/271.9.
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