Methyl iodide → HCID 66609653, compound

Participants

Reaction Conditions

Reaction Steps

Methyl iodide (0.01 mL, 0.161 mmol) was added to a suspension of a 60% dispersion of sodium hydride in mineral oils (3.85 mg, 0.096 mmol) and 5-(1H-Indol-2-ylcarbonyl)-2-(phenoxymethyl)-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridine (0.03 g, 0.08 mmol) in DMF (2 mL). The mixture was stirred under microwave irradiation at 100° C. for 10 minutes. Then a 60% dispersion of sodium hydride in mineral oils (3.86 mg, 0.096 mmol) and methyl iodide (0.01 mL, 0.161 mmol) were added. The crude product was washed with a saturated solution of sodium hydrogen carbonate and extracted with diethyl ether. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by RP HPLC on (C18 XBridge 19×100 5 um). Mobile phase (Gradient from 80% 0.1% NH4CO3H/NH4OH pH 9 solution in Water, 20% ACN to 0% 0.1% NH4CO3H/NH4OH pH 9 solution in Water, 100% ACN). The solvents were evaporated to yield 5-[(1-methyl-1H-indol-2-yl)carbonyl]-2-(phenoxymethyl)-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridine (17.25 mg, 55% yield) as a white solid. C23H21N3O3 1H NMR (500 MHz, CDCl3) δ ppm 2.82 (br. t, J=5.3 Hz, 2 H), 3.87 (s, 3 H), 4.05 (br. t, J=5.2 Hz, 2 H), 4.87 (s, 2 H), 5.14 (s, 2 H), 6.71 (s, 1 H), 6.98-7.07 (m, 3 H), 7.18 (t, J=7.4 Hz, 1 H), 7.29-7.37 (m, 3 H), 7.39 (d, J=8.4 Hz, 1 H), 7.66 (d, J=8.1 Hz, 1 H).

Provenance & Evidence