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【结 构 式】

【分子编号】29304

【品名】4-(7-bromo-5-methoxy-1-benzofuran-2-yl)-1-methylpyridinium (sulfonatooxy)methane

【CA登记号】

【 分 子 式 】C16H16BrNO6S

【 分 子 量 】430.27618

【元素组成】C 44.66% H 3.75% Br 18.57% N 3.26% O 22.31% S 7.45%

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:(V)

Bromination of 2-hydroxy-5-methoxybenzaldehyde (I) in acetic acid / sodium acetate mixture gives bromoaldehyde (II). Condensation to the benzofuranylpyridine (IV) is achieved by heating a solution of (II) and 4-(chloromethyl)pyridine hydrochloride (III) in polyethylene glycol-400 in the presence of potassium carbonate. Quaternization of (IV) with dimethylsulfate in dichloromethane affords (V), which upon reduction with sodium borohydride gives intermediate (VI). Reduction of (VI) with platinum on charcoal in methanol/HBr solution yields the N-methylpiperidine (VII). Degradation of the N-methyl group with ethylchloroformate in toluene affords the carbamate (VIII). Final treatment of (VIII) with potassium hydroxide in n-butanol yields the free base of brofaremine, which is converted to its hydrochloride salt by treatment with hydrochloric acid in methanol.

1 Schenker, K.; Bernasconi, R. (Novartis AG); Tetrahydropyridine and piperidine derivatives and processes for the preparation thereof. DE 2653147; ES 453582; FR 2332754; GB 1565055; JP 52065277 .
2 Waldmeier, P.C.; Schilling, W.; Brofaremine Hydrochloride. Drugs Fut 1985, 10, 5, 371.
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) 29301 2-hydroxy-5-methoxybenzaldehyde 672-13-9 C8H8O3 详情 详情
(II) 29302 3-bromo-2-hydroxy-5-methoxybenzaldehyde C8H7BrO3 详情 详情
(III) 10844 4-(Chloromethyl)pyridine 10445-91-7 C6H6ClN 详情 详情
(IV) 29303 4-(7-bromo-5-methoxy-1-benzofuran-2-yl)pyridine C14H10BrNO2 详情 详情
(V) 29304 4-(7-bromo-5-methoxy-1-benzofuran-2-yl)-1-methylpyridinium (sulfonatooxy)methane C16H16BrNO6S 详情 详情
(VI) 29305 4-(7-bromo-5-methoxy-1-benzofuran-2-yl)-1-methyl-1,2,3,6-tetrahydropyridine C15H16BrNO2 详情 详情
(VII) 29306 4-(7-bromo-5-methoxy-1-benzofuran-2-yl)-1-methylpiperidine C15H18BrNO2 详情 详情
(VIII) 29307 ethyl 4-(7-bromo-5-methoxy-1-benzofuran-2-yl)-1-piperidinecarboxylate C17H20BrNO4 详情 详情
(IX) 11229 1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate 541-41-3 C3H5ClO2 详情 详情
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