Some common heterocyclic compound, 26663-77-4, name is Methyl benzimidazole-5-carboxylate, molecular formula is C9H8N2O2, 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. SDS of cas: 26663-77-4
Methyl lH-benzo[d]imidazole-5-carboxylaie (528 mg, 3 mrnol) in lOmL of DMF was added NaH (160 mg, 6 mmol) at 0C under 2, then the mixture was stirred at (TC for 30 min, then a solution of tert-butyl 4′-(bromomethyl)biphenyl- 2-carboxylate (1.09 g, 3.15 mmol) in DMF (5 mL) was added dropwise at 0C to the reaction mixture, then the mixture was stirred at RTovernight. The mixture was poured into 50 mL of water. The mixtitre was extracted with EtOAc (30 ml_x3) and washed with water (20 mL) and brine (20mL), dried over Na2S04, filtered, and concentrated. The crude product was purified with Combiflash (hexane/EtOAc = 2/1, silica gel) to obtain the titled compound 1. ? NMR (CHLOROFORM-d) delta 8.57 (s, 1H), 8.13 (s, 3H), 7.98 – 8.06 (m, 5H), 7.75 – 7.82 (m, 2H), 7.46 – 7.53 (m, 2H), 7.37 – 7.44 (m, 4H), 7.22 – 7.35 (m, 14H), 5.49 (s, 2H), 5.46 (s, 3H), 3.96 (s, M l ). 3.95 (s, 3H), 1.19 (d, J – 9.7 Hz, 22H); Step B: l -((2′-(tert-butoxycarbonyl)-[l , i ‘~biphenyl]~4-yl)raetliyl)- lH- benzo[d]imidazole-5-carboxy1ic acid, 1 -((2’-(tert-butoxycarbonyl)- [ 1 , Gamma- biphenyl]-4-yl)methyl)- lH-benzo[d]imidazole-6-carboxylic acid The mixture 1 (from Step A) (300 mg, 0.68 mmol) and LiOH (83 mg, 2.04 mmol) in methanol (5 mL) and H?0 (2 mL) was stirred at RT for 18 h. Methanol was removed under the reduced pressure, then PH was adjusted to 6 with IN HCl. A gradual formation of precipitate was observed and filtered. The filter cake was washed by water (10 mL). The residue was separated and purified with Prep-TLC (PE/EtOAc = 112, silica gel) to give the titled compound 2 and 3. 2 ? NMR (CHLOROFORM-d) : 8.26 (s, 2H), 7.75 7.84 (m, 1H), 7.47 ¡¤ 7.54 (m, l H), 7.38 – 7.44 (m, 1 H), 7.29 – 7.36 (m, 5H), 5.52 (s, 2H), 1 .19 (s, 9H) 3 T NMR (CHLOROFORM-d) delta: 8.76 (s, 1H), 8.31 fs, 1H), 7.77 – 7.85 (m, 1H), 7.38 – 7.54 (m, 4H), 7.33 (t, J = 8.2 Hz, 4H), 5.49 (s, 2H), 1.21 (s, 9H)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 26663-77-4, its application will become more common.
Reference:
Patent; RIPKA, Amy S.; SAUNDERS, Jeffrey O.; KAMENECKA, Theodore Mark; GRIFFIN, Patrick R.; WO2013/78240; (2013); A1;,
Imidazole – Wikipedia,
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