Sodium Carbonate → HCID 57819874, compound

Participants

Reaction Steps

A mixture of N-[(3-bromo-4-methylphenyl)methyl]-N′-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}propanediamide (1.3 g, 2.275 mmol), (3-formylphenyl)boronic acid (0.428 g, 2.85 mmol), tetrakis (triphenylphosphine) palladium (0) (0.093 g, 0.080 mmol), sodium carbonate (0.610 g, 5.76 mmol), and 1,4-dioxane (14 mL) and water (5 mL), while stirring under N2, was microwaved at 140° C. for 30 min. The reaction mixture was diluted with EtOAc and water. The organic layer was recovered and washed with saturated NaCl, dried over Na2SO4, and then evaporated to viscous taffy. The viscous taffy was purified on a Chromatotron Plate Silica Gel (1000μ) eluting with CH2Cl2— MeOH (97:3) to afford N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N′-[(3′-formyl-6-methyl-3-biphenylyl)methyl]propanediamide (69.7 mg, 32.8%) as a viscous, nearly colorless, foam, taffy. LC-MS m/z 597.5 (M+H)+, 0.87 min (ret time).

Provenance & Evidence