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【结 构 式】

【分子编号】51711

【品名】1-(4-fluorobenzyl)-1H-indol-5-yl methyl ether; 1-(4-fluorobenzyl)-5-methoxy-1H-indole

【CA登记号】

【 分 子 式 】C16H14FNO

【 分 子 量 】255.2917032

【元素组成】C 75.28% H 5.53% F 7.44% N 5.49% O 6.27%

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:(II)

The reaction of 5-methoxyindol (I) with 4-fluorobenzyl chloride in DMF gives 5-methoxy-1-(4-fluorobenzyl)indol (II). This compound is acylated with oxalyl chloride, yielding 5-methoxy-[1-(4-fluorobenzyl)indol-3-yl]glyoxylic acid chloride (III), which is transformed with 4-amino-3,5-dichloropyridine into the corresponding amide (IV). The reaction of (IV) with borontribromide in toluene cleaves the methoxy group, yielding AWD 12-281.

1 Hofgen, N.; Schupke, H.; Marx, D.; Gasparic, A.; Kronbach, T.; Hartenhauer, H.; Szelenyi, I.; Krone, D.; Hempel, R.; Kiss, H.; Berthold, K.; Egerland, U.; Olbrich, M.; Heer, S.; Rundfelt, C.; AWD 12-281. Drugs Fut 2002, 27, 2, 111.
2 Höfgen, N.; Kronbach, T.; Plymeropoulos, E.; Marx, D.; Heer, S.; Szelenyi, S.; Egerland, U.; Poppe, H. (Arzneimittelwerk Dresden GmbH); New hydroxyindoles, their use as phosphodiesterase 4 inhibitors and method for producing same. CA 2270301; DE 19818964; WO 9955696 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
12354 4-Fluorobenzyl chloride; 1-(Chloromethyl)-4-fluorobenzene 352-11-4 C7H6ClF 详情 详情
25135 3,5-dichloro-4-pyridinamine; 4-amino-3,5-dichloropyridine 22889-78-7 C5H4Cl2N2 详情 详情
(I) 25902 1H-Indol-5-yl methyl ether; 5-Methoxy-1H-indole; 5-Methoxyindole 1006-94-6 C9H9NO 详情 详情
(II) 51711 1-(4-fluorobenzyl)-1H-indol-5-yl methyl ether; 1-(4-fluorobenzyl)-5-methoxy-1H-indole C16H14FNO 详情 详情
(III) 51712 2-[1-(4-fluorobenzyl)-5-methoxy-1H-indol-3-yl]-2-oxoacetyl chloride C18H13ClFNO3 详情 详情
(IV) 31732 N-(3,5-dichloro-4-pyridinyl)-2-[1-(4-fluorobenzyl)-5-methoxy-1H-indol-3-yl]-2-oxoacetamide C23H16Cl2FN3O3 详情 详情
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