8-Hydroxyquinoline → HCID 58998405, compound

Participants

Reaction Conditions

Reaction Steps

In a dry flask was combined (7-Fluoro-1-oxo-1,2-dihydro-isoquinolin-6-yl)-methyl-carbamic acid tert-butyl ester (Example 45, compound 10, Scheme B) (102 mg, 0.35 mmol), 2-amino-5-iodopyridine (84 mg, 0.38 mmol, 1.1 eq), copper (I) iodide (7 mg, 0.037 mmol, 0.11 eq), 8-hydroxyquinoline (6 mg, 0.041 mmol, 0.12 eq) and powdered potassium carbonate (58 mg, 0.42 mmol, 1.2 eq). Under Ar atmosphere, dry dimethylsulfoxide (DMSO, 1.5 mL) was added, and the mixture was stirred at 115° C. for 50 hr. The reaction was cooled, concentrated and purified by chromatography (silica, 2-15% isopropyl alcohol/dichloromethane) to give 67 mg (50%) of [2-(6-Amino-pyridin-3-yl)-7-fluoro-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester as a grey solid. ES-MS (M+H)+=385. 1H-NMR (DMSO-d) δ (ppm): 1.33 (s, 9), 3.19 (s, 3), 6.25 (br m, NH2), 6.53 (m, 1), 6.64-6.65 (d, 1), 7.37-7.39 (d, 1), 7.44-7.46 (d, 1), 7.77-7.79 (d, 1), 7.87-7.90 (d, 1), 7.95 (m, 1H).

Provenance & Evidence