6-(Morpholino)pyridine-3-boronic Acid (contains varying amounts of Anhydride) → 1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-[6-(4-morpholinyl)-3-pyridinyl]-1H-indazole-4-carboxamide

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Reaction Steps

The title compound was prepared in a similar manner as described for example 8 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-(4-morpholinyl)-3-pyridinyl]boronic acid (70 mg, 0.337 mmol). The final product was collected as a white solid (98 mg, 81%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.46 (br. s., 1H) 8.68 (d, J=2.53 Hz, 2H) 8.37 (s, 1H) 8.07-8.12 (m, 2H) 7.84 (d, J=1.01 Hz, 1H) 6.98 (d, J=8.84 Hz, 1H) 5.91 (s, 1H) 5.14 (quin, J=6.57 Hz, 1H) 4.42 (d, J=4.80 Hz, 2H) 3.71-3.76 (m, 4H) 3.50-3.56 (m, 4H) 2.52-2.56 (m, 2H) 2.13 (s, 3H) 1.51-1.58 (m, 2H) 1.51 (s, 3H) 1.49 (s, 3H) 0.88 (t, J=7.33 Hz, 3H). LC-MS (ES) m/z=529.0 [M+H]+

Provenance & Evidence