Cesium carbonate → Methyl 6-(4-(dimethylamino)piperidin-1-yl)-1-isopropyl-1H-indazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a 10-mL microwave tube were added methyl 6-bromo-1-(1-methylethyl)-1H-indazole-4-carboxylate (200 mg, 0.673 mmol), N,N-dimethyl-4-piperidinamine (95 mg, 0.740 mmol), toluene (3 mL), and cesium carbonate (329 mg, 1.010 mmol), and the mixture was degassed for 5 min by bubbling N2. BINAP (62.9 mg, 0.101 mmol) and Pd2(dba)3 (30.8 mg, 0.034 mmol) were added. The tube was sealed and the mixture was heated at 115° C. with stirring for 15 h. The mixture was diluted with methanol (5 mL) and filtered. The filtrate was concentrated and the residue was purified using reverse-phase HPLC to give 58 mg of product as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.45 (d, J=8.0 Hz, 6H), 1.54-1.61 (m, 2H), 1.87-1.96 (m, 2H), 2.31 (m, 6H), 2.80-2.83 (m, 2H), 3.83-3.86 (m, 2H), 3.93 (s, 3H), 4.98-5.04 (m, 1H), 7.29 (s, 1H), 7.57 (s, 1H), 8.17 (s, 1H). LCMS: (M+H)+=345.2

Provenance & Evidence