3-fluoropyridine -Drug Synthesis Database

【结构式】

【分子编号】46855

【品名】3-fluoropyridine

【CA登记号】372-47-4

【分子式】C₅H₄FN

【分子量】97.0919032

【元素组成】C 61.85% H 4.15% F 19.57% N 14.43%

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：(V)

Acid-catalyzed condensation of 4-nitrophenylhydrazine (I) with 1,1,1,5,5,5-hexafluoro-2,4-pentanedione (II) produced pyrazole (III). Reduction of the nitro group of (III) to the corresponding amine (IV) was achieved either by treatment with stannous chloride or by catalytic hydrogenation over Pd/C. Fluoroisonicotinic acid (VI) was prepared by lithiation of 3-fluoropyridine (V) at -78 C followed by quenching with dry ice. Finally, coupling of acid (VI) with amine (IV) yielded the target amide.

参考文献中间体

合成目标

【1】 Sciotti, R.J.; Wagenaar, F.L.; Zhou, X.; Wiedeman, P.E.; Warrior, U.; Luly, J.R.; Djuric, S.W.; Tu, N.P.; Ba Maung, N.Y.; Madar, D.J.; Gubbins, E.J.; Basha, A. (Abbott Laboratories Inc.); Pyrazole inhibitors of cytokine production. EP 1068187; WO 9951580 .

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)	34400	1-(4-nitrophenyl)hydrazine; 4-Nitrophenylhydrazine	100-16-3	C₆H₇N₃O₂	详情	详情
(II)	50521	Hexafluoroacetylacetone; 1,1,1,5,5,5-Hexafluoro-2,4-pentanedione; 1,1,1,5,5,5-Hexafluoroacetylacetonate; 1,1,1,5,5,5-Hexafluoroacetylacetone; 1,1,1-Hexafluoro-2,4-pentanedione	1522-22-1	C₅H₂F₆O₂	详情	详情
(III)	50522	1-(4-nitrophenyl)-3,5-bis(trifluoromethyl)-1H-pyrazole		C₁₁H₅F₆N₃O₂	详情	详情
(IV)	50523	4-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]phenylamine; 4-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]aniline		C₁₁H₇F₆N₃	详情	详情
(V)	46855	3-fluoropyridine	372-47-4	C₅H₄FN	详情	详情
(VI)	50524	3-fluoroisonicotinic acid		C₆H₄FNO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Lithiation of 3-fluoropyridine (I) followed by formylation with methyl formate afforded aldehyde (II). Porphyrin (IV) was then prepared by condensation of aldehyde (II) with pyrrole (III) in refluxing propionic acid. Methylation of (IV) using methyl p-toluenesulfonate then gave the title pyridinium tosylate salt.

参考文献中间体

合成目标

【1】 Shin, J.-H.; Namgoong, S.K.; Kim, H.-S.; Moon, S.C.; Jeong, B.H.; Lee, B.S.; Yu, B.S.; Lee, J.-S.; Synthesis of tetrakis(multifluoro-4-pyridyl)porphin derivatives as acetylcholinesterase inhibitors. Bioorg Med Chem Lett 2000, 10, 13, 1435.

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)	46855	3-fluoropyridine	372-47-4	C₅H₄FN	详情	详情
(II)	46856	3-fluoroisonicotinaldehyde		C₆H₄FNO	详情	详情
(III)	21674	1H-pyrrole	109-97-7	C₄H₅N	详情	详情
(IV)	46857	2,7,12,17-tetrakis(3-fluoro-4-pyridinyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1(3,6).1(8,11).1(13,16)]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaene		C₄₀H₂₂F₄N₈	详情	详情

Extended Information