8-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole -Drug Synthesis Database

【结构式】

【分子编号】14941

【品名】8-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

【CA登记号】39876-39-6

【分子式】C₁₁H₁₁FN₂

【分子量】190.2202232

【元素组成】C 69.46% H 5.83% F 9.99% N 14.73%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV)

The reaction of 4-fluorophenylhydrazine hydrochloride (I) with N-carbethoxy-4-piperidone (II) under Fisher's conditions affords N2-carbethoxy-8-fluoro-2,3,4,5-tetrahydro-1H-pyridol[4,3-b]indole (III). Treatment of (III) with Claisen's alkali affords the N-2 unsubstituted 8-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (IV), which is finally condensed with 3-pyridinylpropyl bromide hydrobromide (V) in DMF in the presence of triethyl amine (TEA). Compound (V) is obtained by refluxing 3-pyridinylpropanol with 48% hydrobromic acid.

参考文献中间体

合成目标

【1】 Andree, T.H.; Webb, M.B.; Patel, U.R.; Muth, E.A.; Moyer, J.A.; Abou-Gharbia, M.; Antipsychotic activity of substituted gamma-carbol. J Med Chem 1987, 30, 1818.
【2】 Andree, T.; Abou-Gharbia, M.; WY-47384. Drugs Fut 1988, 13, 6, 541.

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)	13486	Ethyl 4-oxo-1-piperidinecarboxylate; N-Carbethoxy-4-piperidone	29976-53-2	C₈H₁₃NO₃	详情	详情
(I)	22135	1-(4-fluorophenyl)hydrazine	371-14-2	C₆H₇FN₂	详情	详情
(III)	22137	ethyl 8-fluoro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate		C₁₄H₁₅FN₂O₂	详情	详情
(IV)	14941	8-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole	39876-39-6	C₁₁H₁₁FN₂	详情	详情
(V)	22139	3-(3-bromopropyl)pyridine		C₈H₁₀BrN	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The reaction of 4-fluorophenylhydrazine, hydrochloride (I) with 4-piperidone hydrochloride hydrate (II) in refluxing ethanol afforded 8-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b] indole (III) in 82% yield. Compound (III) was reacted with 4-vinylpyridine in THF in the presence of acetic acid to give WY-47,791 free base in 85% yield which was converted to the hydrochloride salt.

参考文献中间体

合成目标

【1】 Moyer, J.A.; Andree, T.H.; Abou-Gharbia, M.; Patel, U.A.; Muth, E.A.; Webb, M.B.; Antipsychotic activity of substituted gamma-carbolines. J Med Chem 1987, 30, 1818-23.
【2】 Abou-Gharbia, M.; Marquis, K.; Andree, T.; WY-47,791. Drugs Fut 1991, 16, 11, 1008.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	45857	4-vinylpyridine		C₇H₇N	详情	详情
(I)	14939	4-Fluorophenylhydrazine hydrochloride; 1-(4-fluorophenyl)hydrazine hydrochloride	823-85-8	C₆H₈ClFN₂	详情	详情
(II)	14940	tetrahydro-4,4(1H)-pyridinediol hydrocloride		C₅H₁₂ClNO₂	详情	详情
(III)	14941	8-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole	39876-39-6	C₁₁H₁₁FN₂	详情	详情

Extended Information