4-(3-fluoro-5-sulfanylphenyl)tetrahydro-2H-pyran-4-carbonitrile -Drug Synthesis Database

【结构式】

【分子编号】60260

【品名】4-(3-fluoro-5-sulfanylphenyl)tetrahydro-2H-pyran-4-carbonitrile

【CA登记号】

【分子式】C₁₂H₁₂FNOS

【分子量】237.2978232

【元素组成】C 60.74% H 5.1% F 8.01% N 5.9% O 6.74% S 13.51%

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：(VI)

Alkylation of 3,5-difluorophenylacetonitrile (I) with bis-(2-chloroethyl)ether (II) affords the tetrahydropyran derivative (III). Subsequent displacement of one fluoride group of (III) with sodium methylsulfide in hot DMF yields thioether (IV). Oxidation of (IV) employing NaIO4 leads to sulfoxide (V). Then, Pummerer rearrangement of sulfoxide (V) with trifluoroacetic anhydride, followed by basic hydrolysis, furnishes thiol (VI)

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
(I)	60256	2-(3,5-difluorophenyl)acetonitrile		C₈H₅F₂N	详情	详情
(II)	12060	Bis(2-chloroethyl) ether; 1-Chloro-2-(2-chloroethoxy)ethane; 2,2'-Dichlorodiethyl ether	111-44-4	C₄H₈Cl₂O	详情	详情
(III)	60257	4-(3,5-difluorophenyl)tetrahydro-2H-pyran-4-carbonitrile		C₁₂H₁₁F₂NO	详情	详情
(IV)	60258	4-[3-fluoro-5-(methylsulfanyl)phenyl]tetrahydro-2H-pyran-4-carbonitrile		C₁₃H₁₄FNOS	详情	详情
(V)	60259	4-[3-fluoro-5-(methylsulfinyl)phenyl]tetrahydro-2H-pyran-4-carbonitrile		C₁₃H₁₄FNO₂S	详情	详情
(VI)	60260	4-(3-fluoro-5-sulfanylphenyl)tetrahydro-2H-pyran-4-carbonitrile		C₁₂H₁₂FNOS	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

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