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【结 构 式】

【分子编号】45476

【品名】4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carbonitrile

【CA登记号】

【 分 子 式 】C14H7ClN2OS

【 分 子 量 】286.74116

【元素组成】C 58.64% H 2.46% Cl 12.36% N 9.77% O 5.58% S 11.18%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VIII)

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
Extended Information