As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 3314-30-5 name is 1H-Benzo[d]imidazole-2-carbaldehyde, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 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¡ãC, 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, 3-(2-aminoethyl)-N-benzylbenzamide hydrochloride (380) (171 mg, 0.59 mmol), 1 H-1 ,3-benzodiazole-5-carbaldehyde (129 mg, 0.88 mmol) and DIPEA (102 muIota, 0.59 mmol) in MeOH (5 ml) at room temperature for 72 h, followed by the addition NaB4 (33 mg, 0.88 mmol) gave the title compound (75 mg, 33percent) as a beige solid after purification by basic prepHPLC followed by trituration with DCM. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.16 (s, 1 H), 8.98 (t, J = 5.9 Hz, 1 H), 7.75 (s, 1 H), 7.73 – 7.69 (m, 1 H), 7.54 – 7.39 (m, 2H), 7.39 – 7.34 (m, 2H), 7.32 – 7.29 (m, 4H), 7.26 – 7.20 (m, 1 H), 7.15 – 7.07 (m, 2H), 4.47 (d, J = 6.0 Hz, 2H), 3.93 (s, 2H), 2.86 – 2.77 (m, 4H)
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Benzo[d]imidazole-2-carbaldehyde, and friends who are interested can also refer to it.
Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Imidazole – Wikipedia,
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