1,4-Dioxane → HCID 178452069, compound

Participants

Reaction Conditions

Reaction Steps

The mixture of [4-[2-(2-bromo-pyridine-4-carbonyl)-3H-imidazo[4,5-b]pyridine-5-yl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester (40 mg, 0.08 mmole), 2-isoquinoline boronic acid (13.8 mg, 0.08 mmole), Pd(Ph3)4 (27.6 mg, 0.24 mmole), 2 molar of K3PO4 aqueous (0.08 ml, 0.16 mmole), and dioxane (3.0 ml) was degassed and heated to 120° C. for 20 minutes in microwave. Reaction solution was diluted with water and extracted with EtOAc. EtOAc layer was concentrated. Residue was purified by using silica gel chromatography, eluting with 50% to 100% of EtOAc in CH2Cl2 to afford [4-[2-(2-isoquinolin-4-yl-pyridine-4-carbonyl)-3H-imidazo[4.5-b]pyridine-5-yl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester (15 mg, 34%). 1H NMR (400 MHz, CD2Cl2) δ 1.27 (d, 9H), 1.89 (m, 2H), 325 (m, 2H), 3.51 (m, 2H), 3.66 (m, 2H), 3.78 (m, 2H), 6.65 (d, J=9.03 Hz, 1H), 7.61 (t, J=7.53 Hz, J=7.53 Hz, 1H), 7.69 (t, J=7.53 Hz, J=7.53 Hz, 1H), 7.84 (d, J=9.03 Hz, 1H), 8.03 (d, J=8.03 Hz, 1H), 8.27 (d, J=8.03 Hz, 1H), 8.39 (d, J=4.52 Hz, 1H), 8.66 (s, 1H), 8.71 (s, 1H), 8.95 (d, J=5.02 Hz, 1H), 9.28 (s, 1H). HR-MS m/z 550.2570 [M+1].

Provenance & Evidence