Electric Literature of 68282-53-1, These common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
COMPOUND 12.1. 57: NV-DIETHYL-4-f 5, 6, 7-TRIMETHOXY-2-r (4-METHYL- lH-IMIDAZOL-5-YL) METHYLl-1, 2 3, 4-TETRAHYDROISOQUINOLIN-1- YL}BENZAMIDE; 4-Methyl-imidazole-5-carboxyaldehyde (65.2 mg, 0.59 mmol) was added to a solution of INTERMEDIATE 5.1. 16 (117.9 mg, 0.30 mmol) in 1,2-dichloroethane (5 mL) and the reaction mixture stirred at room temperature for 10 min. Sodium triacetoxyborohydride (439 mg, 2.07 mmol) was added followed by N-methyl-2- pyrrolidinone (350, uL) and the reaction mixture stirred at RT for 16 h. 1 N NaOH (5 mL) was added and the organic solvent removed in vacuo. The residue was extracted with EtOAc (3 x 20 mL) and the organic layer washed with water (20 mL). The organic layer was concentrated in vacuo and the residue purified by flash chromatography on Si02 column (EtOAc: MeOH 95: 5) to afford COMPOUND 12.1. 57 as an oil (32.2 mg, 22%).’HNMR (500 MHz, CDCl3) : 8 1.11 (br s, 3H), 1.25 (br s, 3H), 2. 09 (s, 3H), 2.52 (m, 1H), 2.70 (dt, J6.5, 17 Hz, 1H), 2 : 81 (dt, J4. 5, 17 Hz, 1H), 3.05 (m, 1H), 3.27 (br s, 2H), 3.39 (m, 2H), 3.55 (br s, 1H), 3.59 (m, 1H), 3.60 (s, 3H), 3.85 (s, 3H), 3.89 (s, 3H), 4.56 (s, 1H), 6.00 (s, 1H), 7.28-7. 32 (m, 4H), 7.39 (s, 1H) ; 13C NMR (125 MHz, CDC13) : 6 11. 12, 13.11, 14.41, 22.43, 39.69, 43.65, 46.30, 49.22, 56.12, 60. 71, 61.03, 67.59, 107.92, 121. 56,126. 55,129. 87, 130. 31, 132.67, 133.31, 136.29, 140.75, 145.12, 150. 85, 151. 79,171. 51; (+) LRESIMS m/z 493.24 [M+H] +.
Statistics shows that 5-Methyl-1H-imidazole-4-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 68282-53-1.