(R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine -Drug Synthesis Database

【结构式】

【分子编号】68695

【品名】(R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

【CA登记号】　

【分子式】C₁₉H₂₂BCl₂FN₂O₃

【分子量】427.11

【元素组成】C 53.43% H 5.19% B 2.53% Cl 16.60% F 3.45% N 6.56% O 11.24%

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：(V)

Reaction of 5-bromo-3-[1(R)-(2,6-dichloro-3-fluorophenyl)ethyl]-pyridin-2-amine (I) with Boc2O by means of DMAP in DMF gives the protected aniline (II), which is condensed with bis(pinacolato)-diboron (III) by means of a Pd catalyst and KOAc in DMSO to yield the N-protected boronic ester (IV). Deprotection of the amino group of compound (IV) by means of HCl in dioxane/dichloromethane affords the boronic ester (V), which is condensed with 1-(1-Boc-piperidin-4-yl)-4-bromo-1H-pyrazole (VI) by means of PdCl2(PPh3)2 and Na2CO3 in hot DME/water to provide the adduct (VII). Finally, this compound is N-deprotected by means of HCl in dioxane/dichloromethane, as before .

参考文献中间体

合成目标

【1】 Cui, J.J., Funk, L.A., Jia, L. et al. (Pfizer, Inc.; Agouron Pharmaceuticals, Inc.). Enantiomerically pure aminoheteroaryl compounds as protein kinase inhibitors. EP 1786785, JP 2008510790, US 2006046991, WO 2006021884.
【2】 Cui, J.J., Funk, L.A., Jia, L. et al. (Pfizer, Inc.). Pyrazole-substituted aminoheteroaryl compounds as protein kinase inhibitors. EP 1784396, JP 2008510788, WO 2006021881.

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)	68698	5-bromo-3-[1(R)-(2,6-dichloro-3-fluorophenyl)ethyl]-pyridin-2-amine;(R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine		C₁₃H₁₀BrCl₂FN₂O	详情	详情
(II)	68697			C₂₃H₂₆BrCl₂FN₂O₅	详情	详情
(III)	53342	4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; Bis(pinacolato)diboron; Diboron pinacol ester	73183-34-3	C₁₂H₂₄B₂O₄	详情	详情
(IV)	68696			C₂₉H₃₈BCl₂FN₂O₇	详情	详情
(V)	68695	(R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine		C₁₉H₂₂BCl₂FN₂O₃	详情	详情
(VI)	68694	1-(1-Boc-piperidin-4-yl)-4-bromo-1H-pyrazole;4-(4-Bromopyrazol-1-yl)piperidine-1-carboxylicacid tert-butyl ester	877399-50-3	C₁₃H₂₀BrN₃O₂	详情	详情
(VII)	68693	(R)-tert-butyl 4-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate		C₂₆H₃₀Cl₂FN₅O₃	详情	详情

Extended Information