Sodium hydride → HCID 59577440, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 60% NaH (68 mg, 1.7 mmol) in DMF (2.5 mL) at 0° C. was added a solution of 3,4-dihydro-1H-quinolin-2-one (208 mg, 1.4 mmol) in DMF (2.0 mL). The reaction mixture was stirred (0° C., 30 min) before the addition of 2-(3-chloromethyl-benzofuran-6-yloxy)-thiazolo[4,5-b]pyridine hydrochloride (50 mg, 0.14 mmol). The reaction mixture was stirred (rt, 30 min), washed with water, extracted with ethyl acetate, dried, filtered and concentrated. The residue was purified by reverse phase HPLC to provide the title compound (22 mg, 36%). MS (ESI): mass calcd. for C24H17N3O3S, 427.10; m/z found, 428.0 [M+H]+. 1H NMR (500 MHz, CD3OD): 8.54-8.48 (m, 1H), 8.43-8.36 (m, 1H), 7.88-7.81 (m, 1H), 7.78 (d, J=8.5, 1H), 7.64 (d, J=2.1, 1H), 7.44-7.38 (m, 2H), 7.36-7.30 (m, 1H), 7.30-7.16 (m, 2H), 7.05-6.98 (m, 1H), 5.38 (s, 2H), 2.98-2.85 (m, 2H), 2.79-2.70 (m, 2H).

Provenance & Evidence