Sodium Carbonate → HCID 67072591, compound

Participants

Reaction Steps

A mixture of N-{(1S)-2,2-dimethyl-1-[((1S,4S)-5-{[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]carbonyl}-2,5-diazabicyclo[2.2.1]hept-2-yl)carbonyl]propyl}-1H-indole-2-carboxamide (150 mg, 0.26 mmol), 2-bromo-3-fluoropyridine (69 mg, 0.38 mmol), Pd(dppf)Cl2 (15 mg, 0.018 mmol), sodium carbonate (55 mg, 0.52 mmol) in dry 1,4-dioxane (2 mL) and water (1 mL) was refluxed for 16 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 (21 mg) as a pale brown solid. LCMS (m/z): 555.3 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm: 0.90-1.10 (m, 9H), 1.80-2.25 (m, 2H), 3.50-4.30 (m, 4H), 4.15-5.10 (m, 3H), 7.00-7.75 (m, 8H), 7.95-8.70 (m, 3H), 9.00-9.30 (m, 1H), 9.40-9.70 (m, 1H)

Provenance & Evidence