Nitrogen → HCID 67467226, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6-bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide (0.15 g, 0.359 mmol), phenylboronic acid (0.088 g, 0.719 mmol) and potassium phosphate (tribasic) (0.229 g, 1.078 mmol) was added 1,4-dioxane (3 mL) and water (0.75 mL). The suspension was degassed with N2 for 10 min, at which time PdCl2(dppf)-CH2Cl2 (0.044 g, 0.054 mmol) was added and the sealed reaction heated at 100° C. overnight. Diluted reaction with EtOAc and filtered through Celite, washing with EtOAc and concentrating in vacuo to a residue that was dissolve in a minimum amount of DCM. Purification by silica gel chromatography (12 gram Isco GOLD silica column; Gradient B: 5-80%; A: dichloromethane, B: 10% (2 M ammonia in methanol) in chloroform) gave N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-phenyl-1H-indazole-4-carboxamide (0.105 g, 0.248 mmol, 69.1% yield). 1H NMR (400 MHz, DMSO-d6) ppm 1.50 (d, J=6.57 Hz, 6H) 2.12 (s, 3H) 2.22 (s, 3H) 4.39 (d, J=4.80 Hz, 2H) 5.10-5.24 (m, 1H) 5.89 (s, 1H) 7.37-7.46 (m, 1H) 7.48-7.55 (m, 2H) 7.82-7.93 (m, 3H) 8.12 (s, 1H) 8.38 (s, 1H) 8.66 (t, J=4.93 Hz, 1H) 11.54 (s, 1H). MS(ES) [M+H]+ 415.1.

Provenance & Evidence