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With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine at 80℃; for 16h;
2 Step 2.
Into a 100-mL pressure tank reactor, was placed 6-bromo-1H-indazol-3-amine (6.50 g, 30.65 mmol, 1.00 equiv), CH3OH (65 mL), Pd(dppf)Cl2(2.24 g, 3.07 mmol, 0.10 equiv), triethylamine (9.31 g, 91.959 mmol, 3.00 equiv), CO(10 atm) . The resulting solution was stirred for 16 hr at 80 °C in an oil bath. The resulting mixture was concentrated. The resulting solution was diluted with 100 mL of H2O. The resulting solution was extracted with 3x60 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2x60 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1). This resulted in 3.5 g (59.7%) of methyl 3-amino-1H-indazole-6-carboxylate as a brown solid. LCMS: [M+H]+=192.
With dmap; triethylamine In dichloromethane at 20℃; for 16h;
3 Step 3.
Into a 250-mL 3-necked round-bottom flask, was placed methyl 3-amino-1H- indazole-6-carboxylate (3.50 g, 18.31 mmol, 1.00 equiv), DCM (70.0 mL), Boc2O (11.99 g, 54.94 mmol, 3.00 equiv), triethylamine (7.41 g, 73.226 mmol, 4 equiv), DMAP (0.22 g, 1.831 mmol, 0.1 equiv). The resulting solution was stirred for 16 hr at room temperature. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 60 mL of H2O. The resulting solution was extracted with 3x60 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2x60 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:3). This resulted in 3 g (41.9%) of 1-tert- butyl 6-methyl 3-[(tert-butoxycarbonyl)amino]indazole-1,6-dicarboxylate as a brown solid. LCMS: [M+H]+=492.
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