Sodium hydride → HCID 44247543, compound

Participants

Reaction Conditions

Reaction Steps

In a 10 mL vial, 2-((1H-indol-3-yl)sulfinyl)-N-(5-methylisoxazol-3-yl)acetamide (50.0 mg, 0.165 mmol) from Step D was dissolved in DMF (5 mL) and cooled to 0° C. Sodium hydride (60% by weight, 13.0 mg, 0.330 mmol) was then added in one portion and the reaction mixture vigorously stirred at 0° C. for 15 minutes. 3-chloro-benzylbromide (21.6 μL, 0.165 mmol) was added in one portion and the reaction mixture was stirred while being allowed to warm to ambient temperature over 3 hours. The reaction mixture was quenched with water (2 mL) and the solution was extracted with ethyl acetate (3×2 mL). The combined organics were dried over magnesium sulfate and concentrated in vacuo to give an oily residue which was purified on a silica gel column (0-50% ethyl acetate:hexanes over 19 min) to yield the title compound (24 mg, 0.056 mmol, 34% yield). LCMS>98% 220 nm, RT=1.26 min, m/z=428 (m+1). 1H NMR (400 MHz, DMSOD6) 11.32 (s, 1H), 8.19 (s, 1H), 8.00 (d, J=7.8 Hz, 1H), 7.61 (d, J=8.2 Hz, 1H), 7.38 (s, 1H), 7.21-7.36 (m, 4H), 7.15 (d, J=7.2 Hz, 1H), 6.61 (s, 1H), 5.52 (s, 2H), 4.58 (d, J=13.1 Hz, 1H), 4.14 (d, J=13.1 Hz, 1H), 2.38 (s, 3H).

Provenance & Evidence