Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, A new synthetic method of this compound is introduced below., SDS of cas: 3314-30-5
General procedure: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0°C, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10percent MeOH / DCM) afforded the title compound (1.4 g, 38percent, 90percent purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 – 7.49 (m, 2H), 7.29 – 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion using general procedure 3, 1-(2-aminoethyl)-N-[(3-fluoropyridin-2-yl)methyl]-3,5- dimethyl-1 H-pyrazole-4-carboxamide dihydrochloride (262) (150 mg, 0.384 mmol), 1 H-benzimidazole-2- carbaldehyde (73 mg, 0.499 mmol), DIPEA (0.268 ml, 1.537 mmol) and MgSQ (100 mg) in MeOH (7 ml) at room temperature for 16 h, followed by addition of NaBH^ (22 mg, 0.576 mmol) gave the title compound (14 mg, 9percent) as a yellow solid after purification by basic prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.16 (s, 1 H), 8.40 – 8.37 (m, 1 H), 7.84 (t, J = 5.6 Hz, 1 H), 7.72 – 7.66 (m, 1 H), 7.56 – 7.50 (m, 1 H), 7.46 – 7.42 (m, 1 H), 7.40 (dt, J = 8.4, 4.4 Hz, 1 H), 7.17- 7.09 (m, 2H),4.59 (d, J = 4.3 Hz, 2H), 4.05 (t, J = 6.4 Hz, 2H), 3.92 (s, 2H), 2.90 (t, J = 6.4 Hz, 2H), 2.38 (s, 3H), 2.24 (s, 3H) HPLCMS (Method D): [m/z]: 422.3 [M+H]+
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.