Iodoethane → HCID 66906316, 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 (114 mg, 0.381 mmol) (Example 33c) in DMF (6 mL) at −10° C. is added NaH [60% dispersion in oil (20 mg, 0.5 mmol)]. The reaction is stirred at −10° C. for 10 min, placed at room temperature for 5 min, and then recooled to −10° C., at which time ethyl iodide (0.070 mL, 0.875 mmol) is added. After 45 min the reaction is quenched with saturated aqueous NH4Cl, diluted with ethyl acetate and saturated aqueous NaHCO3. The layers are separated and the aqueous layer is extracted two more times with ethyl acetate. The combined organic layers are dried over Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 1:7 to 1:0) to afford 3-(2-ethyl-3,3-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinolin-4-yl)-3H-imidazole-4-carboxylic acid methyl ester; HRMS: (ESI) m/z 328.1673 [(M+H)+: Calcd for C18H22N3O3: 328.1661]; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.21 (t, J=7.1 Hz, 3 H), 1.24 (s, 3 H), 1.40 (s, 3 H), 3.47-3.57 (m, 1 H), 3.67-3.78 (m, 1H), 3.94 (s, 3 H), 6.56 (s, 1 H), 7.28-7.33 (m, 1 H), 7.42 (s, 1 H), 7.46-7.55 (m, 2 H), 7.77 (s, 1 H), 8.20-8.26 (m, 1 H).

Provenance & Evidence