2-(4-fluorophenyl)-2-[(4-methylphenyl)sulfonyl]acetonitrile -Drug Synthesis Database

【结构式】

【分子编号】40035

【品名】2-(4-fluorophenyl)-2-[(4-methylphenyl)sulfonyl]acetonitrile

【CA登记号】

【分子式】C₁₅H₁₂FNO₂S

【分子量】289.3302232

【元素组成】C 62.27% H 4.18% F 6.57% N 4.84% O 11.06% S 11.08%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VI)

2-Chloronicotinic acid (I) was reduced to alcohol (II) employing borane, generated from NaBH4 and BF3.Et2O. Subsequent oxidation of (II) with N-bromosuccinimide produced aldehyde (III), which was condensed with N-Boc-4-aminopiperidine (IV), yielding imine (V). Addition to (V) of (4-fluorophenyl)-toluenesulfonylmethyl isocyanide (VI) gave rise to imidazole (VII). Then, displacement of the 2-chloro of (VII) by means of aniline (VIII) in the presence of NaH furnished the 2-anilinopyridine derivative (IX). The Boc protecting group of (IX) was finally removed by treatment with trifluoroacetic acid.

参考文献中间体

合成目标

【1】 Adams, J.L.; Gallagher, T.F.; Sisko, J.; Peng, Z.-Q.; Osifo, I.K.; Boehm, J.C. (SmithKline Beecham plc); Imidazole cpds.. EP 0831830; JP 1999513017; US 5658903; WO 9640143 .

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)	40032	2-chloroisonicotinic acid	6313-54-8	C₆H₄ClNO₂	详情	详情
(II)	40033	(2-chloro-4-pyridinyl)methanol	100704-10-7	C₆H₆ClNO	详情	详情
(III)	29234	2-chloroisonicotinaldehyde		C₆H₄ClNO	详情	详情
(IV)	28414	4-Amino-1-N-Boc-piperidine; tert-butyl 4-amino-1-piperidinecarboxylate; N-Boc-4-aminopiperidine	87120-72-7	C₁₀H₂₀N₂O₂	详情	详情
(V)	40034	tert-butyl 4-[[(E)-(2-chloro-4-pyridinyl)methylidene]amino]-1-piperidinecarboxylate		C₁₆H₂₂ClN₃O₂	详情	详情
(VI)	40035	2-(4-fluorophenyl)-2-[(4-methylphenyl)sulfonyl]acetonitrile		C₁₅H₁₂FNO₂S	详情	详情
(VII)	40036	tert-butyl 4-[5-(2-chloro-4-pyridinyl)-4-(4-fluorophenyl)-1H-imidazol-1-yl]-1-piperidinecarboxylate		C₂₄H₂₆ClFN₄O₂	详情	详情
(VIII)	12294	Aniline; Phenylamine	62-53-3	C₆H₇N	详情	详情
(IX)	40037	tert-butyl 4-[5-(2-anilino-4-pyridinyl)-4-(4-fluorophenyl)-1H-imidazol-1-yl]-1-piperidinecarboxylate		C₃₀H₃₂FN₅O₂	详情	详情

Extended Information