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【结 构 式】 
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【分子编号】45475 【品名】4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide 【CA登记号】 |
【 分 子 式 】C14H9ClN2O2S 【 分 子 量 】304.75644 【元素组成】C 55.18% H 2.98% Cl 11.63% N 9.19% O 10.5% S 10.52% |
合成路线1
该中间体在本合成路线中的序号：(VII)Treatment of 3,5-dichloropyridine (I) with methyl formate (II), BuLi and diisopropyl amine (DIPA) in THF provides carboxaldehyde (III), which is converted into ester (VI) by first condensation with 4-chlorophenol (IV) by means of tBuOK in THF followed by cyclization with methyl thioglycolate (V) and Cs2CO3. Methyl ester (VI) reacts with methanolic ammonia to yield carboxamide (VII), which is then treated with trifluoroacetic anhydride (TFAA) in pyridine to furnish carbonitrile (VIII). Finally, (VIII) is converted into the desired compound by reaction with hydroxylamine hydrochloride (NH2OH·HCl) and TEA in EtOH.
| 【1】 Lartey, K.; Gunawardana, I.W.; Stout, D.M.; Bhatia, P.; Patel, M.V.; Staeger, M.A.; Boyd, S.A.; Mort, N.A.; Zhu, G.-D.; McCarty, C.M.; Stewart, A.O.; Arendsen, D.L.; Condroski, K.R.; Freeman, J.C. (Abbott Laboratories Inc.); Cell adhesion-inhibiting antiinflammatory cpds.. WO 9962908 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 35535 | 3,5-dichloropyridine | 2457-47-8 | C5H3Cl2N | 详情 | 详情 |
| (II) | 45474 | methyl formate | 107-31-3 | C2H4O2 | 详情 | 详情 |
| (III) | 35536 | 3,5-dichloroisonicotinaldehyde; 3,5-Dichloropyridine-4-carbaldehyde | 136590-83-5 | C6H3Cl2NO | 详情 | 详情 |
| (IV) | 35543 | 4-chlorophenol | 106-48-9 | C6H5ClO | 详情 | 详情 |
| (V) | 18838 | methyl 2-sulfanylacetate | 2365-48-2 | C3H6O2S | 详情 | 详情 |
| (VI) | 35542 | methyl 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylate | C15H10ClNO3S | 详情 | 详情 | |
| (VII) | 45475 | 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide | C14H9ClN2O2S | 详情 | 详情 | |
| (VIII) | 45476 | 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carbonitrile | C14H7ClN2OS | 详情 | 详情 |