6-(Dimethylamino)pyridine-3-boronic acid → 6-[6-(dimethylamino)-3-pyridinyl]-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide

Participants

Reaction Steps

The title compound was prepared in a similar manner as described for example 13 from 6-bromo-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide (100 mg, 0.225 mmol) and [6-(dimethylamino)-3-pyridinyl]boronic acid (49 mg, 0.292 mmol). The final product was collected as a white solid (49 mg, 44%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.55 (s, 1H) 8.57-8.65 (m, 2H) 8.35 (s, 1H) 8.01-8.06 (m, 2H) 7.83 (s, 1H) 6.76 (d, J=8.84 Hz, 1H) 5.92 (s, 1H) 5.13 (dt, J=13.14, 6.57 Hz, 1H) 4.42 (br. s., 1H) 4.41 (br. s., 1H) 3.09 (s, 6H) 2.54 (m, 2H) 2.14 (s, 3H) 1.51-1.58 (m, 2H) 1.50 (s, 3H) 1.49 (s, 3H) 0.88 (t, J=7.33 Hz, 3H). LC-MS (ES) m/z=487.4 [M+H]+

Provenance & Evidence