1-Iodobenzene -Drug Synthesis Database

【结构式】

【分子编号】26344

【品名】1-Iodobenzene

【CA登记号】591-50-4

【分子式】C₆H₅I

【分子量】204.01017

【元素组成】C 35.32% H 2.47% I 62.2%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(II)

By condensation of 5-methyl-2-(1H)-pyridone (I) with iodobenzene (II) by means of K2CO3 and Copper powder at reflux temperature.

参考文献中间体

合成目标

【1】 Gadekar, S.M.; 5-Methyl-1-phenyl-2-(1H)-pyridone compositions and methods of use. CA 1049411; DE 2555411; US 3974281 .
【2】 Gadekar, S.M.; N-Substituted pyridone and general method for preparing pyridones. US 3839346; ZA 7309472 .
【3】 Castaner, J.; Blancafort, P.; Pirfenidone. Drugs Fut 1977, 2, 6, 396.

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)	33875	5-methyl-2(1H)-pyridinone		C₆H₇NO	详情	详情
(II)	26344	1-Iodobenzene	591-50-4	C₆H₅I	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

A synthesis of [14C]-labeled SR-57746A has been described: The iodination of [14C6]-benzene (I) with nitric acid/I2 gives iodobenzene (II), which is treated with sodium trifluoroacetate and CuI yielding trifluoromethylbenzene (III). The nitration of (III) with sodium nitrate affords 3-(trifluoromethyl)nitrobenzene (IV), which is reduced with Fe/HCl to the corresponding aniline (V). The reaction of (V) with tert-butyl nitrite and CuBr2 provides 3-(trifluoromethyl)bromobenzene (VI), which is treated with Mg in THF affording the corresponding Grignard reagent (VII). The condensation of (VII) with piperidone (VIII) gives the piperidol (IX), which is finally dehydrated in acidic medium. In order to aviod radioactive contamination during the purification of compounds iodobenzene (II) and trifluoromethylbenzene (III) by liquid chromatography, a safer route using less volatile compounds has been developed: The nitration of [14C6]-benzene (I) with nitric acid gives nitrobenzene (X), which is iodinated with IPy2BF4/CF3SO3H yielding 3-iodonitrobenzene (XI). Finally, this compound is trifluoromethylated with CF3SiMe3, CuI and KF to provide 3-(trifluoromethyl)nitrobenzene (IV) already reported.

参考文献中间体

合成目标

【1】 Robic, N.; Noel, J.P.; Synthesis of [trifluoromethyl-[C-14(6)]-phenyl] SR 57746A. J Label Compd Radiopharm 1999, 42, 2, 109.

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)	13364	Benzene	71-43-2	C₆H₆	详情	详情
(I)	45201	benzene		C₆H₆	详情	详情
(II)	26344	1-Iodobenzene	591-50-4	C₆H₅I	详情	详情
(II)	45202	1-iodobenzene		C₆H₅I	详情	详情
(III)	26345	1-(Trifluoromethyl)benzene	98-08-8	C₇H₅F₃	详情	详情
(III)	45203	1-(trifluoromethyl)benzene		C₇H₅F₃	详情	详情
(IV)	26346	1-nitro-3-(trifluoromethyl)benzene	98-46-4	C₇H₄F₃NO₂	详情	详情
(IV)	45204	1-nitro-3-(trifluoromethyl)benzene		C₇H₄F₃NO₂	详情	详情
(V)	26347	3-(trifluoromethyl)phenylamine; 3-(trifluoromethyl)aniline; 3-aminobenzotrifluoride	98-16-8	C₇H₆F₃N	详情	详情
(V)	45205	3-(trifluoromethyl)phenylamine; 3-(trifluoromethyl)aniline		C₇H₆F₃N	详情	详情
(VI)	26348	1-bromo-3-(trifluoromethyl)benzene; 3-Bromobenzotrifluoride	401-78-5	C₇H₄BrF₃	详情	详情
(VI)	45206	1-bromo-3-(trifluoromethyl)benzene		C₇H₄BrF₃	详情	详情
(VII)	12028	Bromo[3-(trifluoromethyl)phenyl]magnesium	402-26-6	C₇H₄BrF₃Mg	详情	详情
(VII)	45207	bromo[3-(trifluoromethyl)phenyl]magnesium		C₇H₄BrF₃Mg	详情	详情
(VIII)	26349	1-[2-(2-naphthyl)ethyl]-4-piperidinone		C₁₇H₁₉NO	详情	详情
(IX)	26350	1-[2-(2-naphthyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-4-piperidinol		C₂₄H₂₄F₃NO	详情	详情
(IX)	45208	1-[2-(2-naphthyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-4-piperidinol		C₂₄H₂₄F₃NO	详情	详情
(X)	22523	1-nitrobenzene	28250-14-8	C₆H₅NO₂	详情	详情
(X)	45209	1-nitrobenzene		C₆H₅NO₂	详情	详情
(XI)	26352	3-Iodonitrobenzene; 1-iodo-3-nitrobenzene	645-00-1	C₆H₄INO₂	详情	详情
(XI)	45210	1-iodo-3-nitrobenzene		C₆H₄INO₂	详情	详情

合成路线3

该中间体在本合成路线中的序号：(IV)

5-Methyl-2-nitrophenol (I) was protected as the benzyl ether (II) employing benzyl bromide and NaOH in DMSO. Reduction of the nitro group of (III) with iron and ammonium chloride afforded aniline (III), which was subsequently coupled with iodobenzene (IV) to furnish the diaryl amine (V). Cyclization of (V) in the presence of Pd(OAc)2 in refluxing AcOH gave rise to carbazole (VI). The benzyl group of (VI) was then removed by catalytic hydrogenation over Pd/C to yield phenol derivative (VII). Finally, the title compound was obtained by oxidative coupling of the phenolic monomer (VII) with di-tert-butyl peroxide in boiling chlorobenzene.

参考文献中间体

合成目标

【1】 Zhang, A.; Lin, G.; The first synthesis of optically pure biscarbazoles and determination of their absolute configurations. Tetrahedron Lett 1999, 40, 2, 341.

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)	42182	5-methyl-2-nitrophenol	700-38-9	C₇H₇NO₃	详情	详情
(II)	42183	benzyl 5-methyl-2-nitrophenyl ether; 2-(benzyloxy)-4-methyl-1-nitrobenzene		C₁₄H₁₃NO₃	详情	详情
(III)	42184	2-(benzyloxy)-4-methylaniline; 2-(benzyloxy)-4-methylphenylamine		C₁₄H₁₅NO	详情	详情
(IV)	26344	1-Iodobenzene	591-50-4	C₆H₅I	详情	详情
(V)	42185	N-[2-(benzyloxy)-4-methylphenyl]-N-phenylamine; 2-(benzyloxy)-4-methyl-N-phenylaniline		C₂₀H₁₉NO	详情	详情
(VI)	42186	benzyl 3-methyl-9H-carbazol-1-yl ether; 1-(benzyloxy)-3-methyl-9H-carbazole		C₂₀H₁₇NO	详情	详情
(VII)	42187	3-methyl-9H-carbazol-1-ol		C₁₃H₁₁NO	详情	详情

Extended Information