Water → N-((1S)-1-{[(1S,4S)-5-({5-[4-(dimethylamino)phenyl]-2-pyridinyl}carbonyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]carbonyl}-2,2-dimethylpropyl)-1H-indole-2-carboxamide

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Reaction Conditions

Reaction Steps

A mixture of N-[(1S)-1-({(1S,4S)-5-[(5-bromo-2-pyridinyl)carbonyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)-2,2-dimethylpropyl]-1H-indole-2-carboxamide (100 mg, 0.186 mmol), [4-(dimethylamino)phenyl]boronic acid (31 mg, 0.186 mmol), Pd(Ph3P)4 (10 mg, 0.009 mmol), potassium carbonate (26 mg, 0.186 mmol) in toluene (6 mL), ethanol (2 mL), and water (0.5 mL) was heated to 80° C. for 10 h under a nitrogen atmosphere. The solution was concentrated and the resulting residue was purified by reverse phase HPLC. Concentration of the desired fractions containing product afforded the title compound (45 mg) as a pale brown solid. LCMS (m/z): 579.3 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm: 0.90-1.20 (m, 9H), 1.80-2.20 (m, 2H), 2.90-3.15 (m, 6H), 3.50-4.20 (m, 4H), 4.60-5.60 (m, 4H), 6.90-7.70 (m, 9H), 7.80-8.10 (m, 2H), 8.60-8.85 (m, 1H), 9.15-9.45 (m, 1H)

Provenance & Evidence