5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → 6-(6-amino-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 the same manner as described for example 75 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 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine (75 mg, 0.337 mmol). The final product was collected as a white solid (60 mg, 57%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.55 (s, 1H) 8.61 (t, J=4.93 Hz, 1H) 8.45 (d, J=2.27 Hz, 1H) 8.34 (s, 1H) 8.00 (s, 1H) 7.90 (dd, J=8.59, 2.53 Hz, 1H) 7.78 (s, 1H) 6.55 (d, J=8.59 Hz, 1H) 6.10-6.17 (m, 2H) 5.91 (s, 1H) 5.13 (quin, J=6.57 Hz, 1H) 4.42 (br. s., 1H) 4.41 (br. s., 1H) 2.52-2.56 (m, 2H) 2.13 (s, 3H) 1.51-1.57 (m, 2H) 1.50 (s, 3H) 1.48 (s, 3H) 0.88 (t, J=7.33 Hz, 3H). LC-MS (ES) m/z=459.2

Provenance & Evidence