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Home » Uncategorized » Palladium-catalyzed direct C-H ethoxycarbonylation of 2-aryl-1,2,3-triazoles and efficient synthesis of suvorexant

Palladium-catalyzed direct C-H ethoxycarbonylation of 2-aryl-1,2,3-triazoles and efficient synthesis of suvorexant

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Org. Chem. Front., 2018, Advance Article
DOI: 10.1039/C7QO00945C, Research Article
Rui Sang, Yang Zheng, Hailong Zhang, Xiaohua Wu, Qiantao Wang, Li Hai, Yong Wu
Palladium-catalyzed direct ethoxycarbonylation with diethyl azodicarboxylate was developed and its reaction mechanism was explored by using DFT calculations.

Palladium-catalyzed direct C–H ethoxycarbonylation of 2-aryl-1,2,3-triazoles and efficient synthesis of suvorexant

Abstract

Efficient palladium-catalyzed C–H ethoxycarbonylation of 2-aryl-1,2,3-triazoles was developed by using diethyl azodicarboxylate as the esterification reagent. A wide variety of aryl esters containing 1,2,3-triazoles were obtained in moderate to good yields. In addition, density functional theory calculations were used to enhance the mechanistic studies.

str2

3ea

5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoate

Yellow oil, 1H NMR (600 MHz, Chloroform-d) δ 7.81 (s, 2H), 7.69 – 7.57 (m, 2H), 7.41 (d, J = 8.1 Hz, 8 1H), 4.20 (q, J = 7.1 Hz, 2H), 2.45 (s, 3H), 1.15 (t, J = 7.1 Hz, 3H); 13C NMR (100 MHz, Chloroformd) δ 166.8, 138.8, 136.1, 135.3, 132.2, 130.4, 127.2, 124.4, 61.4, 13.9; IR (cm-1): 2923, 2861, 1723, 1509, 1463, 1410, 1366, 1303, 1285, 1269, 1234, 1201, 1108, 1072, 1044, 1021, 962, 952, 158, 824, 778, 734, 630; HRMS (ESI) Calcd. for C12H13N3O2 [M+Na]+ 254.0905, found 254.0904.

To a round bottom flask charged 4-methyl-2-(2H-1,2,3-triazol-2-yl)benzoate (50 mg, 0.22 mmol), KOH (67.2 mg, 1.2 mmol), EtOH (3 ml) and H2O (0.5 ml), and the system was react at 40 oC for 5 h, and then cooled down to ambient temperature. The pH was adjusted to 1 with 5% HCl, and EtOH was removed under reduced pressure. The residual solvent was extracted with EtOAc (3 x 10 ml), and the solvent was evaporated under reduced pressure. The oily residue was purified by chromatography on a silica gelcolumn (DCM/MeOH) and product 4 was obtained with 90% yield. Suvorexant was synthesised from 4 and 5 according to the literature as previous report. [4, 5] Product 4: 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid: 1H NMR (400 MHz, Chloroform-d) δ 7.83 (s, 2H), 7.76 (d, J = 2.0 Hz, 1H), 7.64 (d, J = 8.2 Hz, 1H), 7.50 – 7.42 (m, 1H), 2.47 (s, 3H). [4, 5] Suvorexant: 1H NMR (400 MHz, Chloroform-d) δ 7.90−7.75 (m, 3H), 7.68-7.01 (m, 5H), 5.09 – 4.46 (m, 1H), 4.23 – 3.41 (m, 6H), 3.16-2.31 (m, 4H), 2.20 – 2.01 (m, 1H), 1.91 – 1.16 (m, 3H); [4, 5]

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Suvorexant.svg

suvorexant

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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 30 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 30 year tenure till date Dec 2017, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 50 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 19 lakh plus views on New Drug Approvals Blog in 216 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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