Methyl iodide → HCID 57781146, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(3,3-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinolin-4-yl)-3H-imidazole-4-carboxylic acid methyl ester (55 mg, 0.184 mmol) in DMF (3.7 mL) at −10° C. is added sodium hydride (60% dispersion in oil 10 mg, 0.25 mmol). The reaction is stirred for 5 min at −10° C. and then placed at room temperature for 10 min. The resulting red solution is re-cooled to −10° C. and methyl iodide (0.025 mL, 0.40 mmol) is added dropwise. The reaction is placed at room temperature. After 10 min the yellow reaction mixture is quenched by the addition of saturated aqueous NH4Cl (ca. 1 mL). The resulting mixture is diluted with ethyl acetate and saturated aqueous NaHCO3. The layers are separated and the aqueous layer is extracted twice with ethyl acetate (ca. 10 mL). The organic layers are combined, dried with Na2SO4, filtered and concentrated in vacuo to afford 3-(2,3,3-trimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinolin-4-yl)-3H-imidazole-4-carboxylic acid methyl ester as a yellow foam requiring no further purification prior to the next transformation; HRMS (ES) m/z 300.1354 [(M+H)+; calculated for C16H18N3O3: 340.1348]; 1H NMR (400 MHz, MeOD) δ ppm 1.30 (s, 3H), 1.41 (s, 3 H), 3.10 (s, 3 H), 4.04 (br. s., 3 H), 6.85 (br. s., 1 H), 7.50 (br. s., 1 H), 7.61-7.73 (m, 2 H), 8.09-8.27 (m, 3 H).

Provenance & Evidence