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【结 构 式】 
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【分子编号】35541 【品名】3,5-bis(4-chlorophenoxy)isonicotinaldehyde 【CA登记号】 |
【 分 子 式 】C18H11Cl2NO3 【 分 子 量 】360.19568 【元素组成】C 60.02% H 3.08% Cl 19.69% N 3.89% O 13.33% |
合成路线1
该中间体在本合成路线中的序号：(IV)The formylation of 3,5-dichloropyridine (I) with methyl formate by means of lithium diisopropylamide (LDA) in THF gives 3,5-dichloropyridine-4-carbaldehyde (II), which is condensed with 4-chlorophenol (III) by means of potassium tert-butoxide in THF yielding 3,5-bis(4-chlorophenoxy)pyridine-4-carbaldehyde (IV). This compound, without isolation is cyclized with methyl thioglycolate (V) by means of Cs2CO3 in DMF affording 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylic acid methyl ester (VI), which is finally condensed with methylamine by means of NaH in DMF to obtain the target amide.
| 【1】 Arendsen, D.L.; Freeman, J.C.; Boyd, S.A.; et al.; Inhibitors of cell adhesion molecule expression in human endothelial cells: Modification of 2-position of 4-aryloxythieno [2,3-c]pyridines. 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 75. |
| 【2】 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) | 35536 | 3,5-dichloroisonicotinaldehyde; 3,5-Dichloropyridine-4-carbaldehyde | 136590-83-5 | C6H3Cl2NO | 详情 | 详情 |
| (III) | 35543 | 4-chlorophenol | 106-48-9 | C6H5ClO | 详情 | 详情 |
| (IV) | 35541 | 3,5-bis(4-chlorophenoxy)isonicotinaldehyde | C18H11Cl2NO3 | 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 |