1-Fluoro-4-iodobenzene; 4-Fluoroiodobenzene; 4-Iodofluorobenzene; p-Fluoroiodobenzene -Drug Synthesis Database

【结构式】

【分子编号】54686

【品名】1-Fluoro-4-iodobenzene; 4-Fluoroiodobenzene; 4-Iodofluorobenzene; p-Fluoroiodobenzene

【CA登记号】352-34-1

【分子式】C₆H₄FI

【分子量】222.0006332

【元素组成】C 32.46% H 1.82% F 8.56% I 57.16%

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：(I)

The reaction of 4-fluoroiodobenzene (I) with 14C-KCN and CuI in refluxing DMF gives 4-fluorobenzonitrile (II), which is reduced with HCO2H and RaNi in DMF to yield 4-fluorobenzaldehyde (III). The condensation of (III) with the substituted ethanolamine (IV) by means of tBu-OK in DMF affords 4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzaldehyde (V), which is condensed with thiazolidine-2,4-dione (VI) by means of piperidine acetate in refluxing toluene to provide the benzylidene-thiazolidinedione (VII). Finally this compound is hydrogenated with H2 over Pd/C in DMF to furnish the target labeled compound.

参考文献中间体

合成目标

【1】 Kirefu, T.; Landwater, S.W.; Latter, A.J.; Lawrie, K.W.M.; Morecombe, D.J.; Willcocks, K.; Rosiglitazone maleate (BRL 49653-C); the preparation of [14C] and [3H] isotopomers. J Label Compd Radiopharm 2001, 44, 5, 329.

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)	54686	1-Fluoro-4-iodobenzene; 4-Fluoroiodobenzene; 4-Iodofluorobenzene; p-Fluoroiodobenzene	352-34-1	C₆H₄FI	详情	详情
(II)	60162	4-fluorobenzonitrile		C₇H₄FN	详情	详情
(III)	60163	4-fluorobenzaldehyde		C₇H₅FO	详情	详情
(IV)	17505	2-[methyl(2-pyridinyl)amino]-1-ethanol		C₈H₁₂N₂O	详情	详情
(V)	60164	4-{2-[methyl(2-pyridinyl)amino]ethoxy}benzaldehyde		C₁₅H₁₆N₂O₂	详情	详情
(VI)	10883	1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione	2295-31-0	C₃H₃NO₂S	详情	详情
(VII)	59997			C₁₈H₁₇N₃O₃S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The reaction of 4-iodofluorobenzene (I) with 14C-labeled potassium cyanide and CuI in DMF at 160 C gives the labeled 4-fluorobenzonitrile (II), which is hydrolyzed with KOH in ethanol/water at 115 C to yield labeled 4-fluorobenzoic acid (III). Finally, this compound is condensed with (3R,4S)-6-acetyl-3-hydroxy-3,4-dihydro-2H-1-benzopyran-4-amine (IV) by means of EDC and HOBT in dichloromethane to afford the target labeled compound.

参考文献中间体

合成目标

【1】 Herdon, H.J.; Jerman, J.C.; Chan, W.N. (GlaxoSmithKline plc); Novel receptor. JP 1998511083; US 5985334; WO 9618650 .

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)	54686	1-Fluoro-4-iodobenzene; 4-Fluoroiodobenzene; 4-Iodofluorobenzene; p-Fluoroiodobenzene	352-34-1	C₆H₄FI	详情	详情
(II)	14144	4-Fluorobenzonitrile	1194-02-1	C₇H₄FN	详情	详情
(II)	54688	4-fluorobenzonitrile		C₇H₄FN	详情	详情
(III)	54687	4-Fluorobenzoic acid	456-22-4	C₇H₅FO₂	详情	详情
(III)	54689	4-fluorobenzoic acid		C₇H₅FO₂	详情	详情
(IV)	28708	1-[(3R,4S)-4-amino-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl]-1-ethanone		C₁₃H₁₇NO₃	详情	详情

合成路线3

该中间体在本合成路线中的序号：(VIII)

Arylation of 2-methylimidazole (VII) with1-fluoro-4-iodobenzene (VIII) gives the iodophenyl imidazole (IX). Then, condensation of aryl iodide (IX) with thiophenol (VI) produces the diaryl sulfide (X). Finally, partial hydrolysis of the cyano group of (X) employing KOH in t-butanol yields the target carboxamide

参考文献中间体

合成目标

【1】 Stevens, R.W.; Mano, T.; Nakao, K.; Okumura, Y. (Pfizer Inc.); 5-Lipoxygenase inhibitors. EP 0787127; JP 1999507322; US 5883106; WO 9611911 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	60260	4-(3-fluoro-5-sulfanylphenyl)tetrahydro-2H-pyran-4-carbonitrile		C₁₂H₁₂FNOS	详情	详情
(VII)	15670	2-Methylimidazole; 2-Methyl-1H-imidazole	693-98-1	C₄H₆N₂	详情	详情
(VIII)	54686	1-Fluoro-4-iodobenzene; 4-Fluoroiodobenzene; 4-Iodofluorobenzene; p-Fluoroiodobenzene	352-34-1	C₆H₄FI	详情	详情
(IX)	60261	1-(4-iodophenyl)-2-methyl-1H-imidazole		C₁₀H₉IN₂	详情	详情
(X)	60262	4-(3-fluoro-5-{[4-(2-methyl-1H-imidazol-1-yl)phenyl]sulfanyl}phenyl)tetrahydro-2H-pyran-4-carbonitrile		C₂₂H₂₀FN₃OS	详情	详情

Extended Information