tert-butyl (3R)-3-[[6-chloro-5-(4-cyanophenyl)-3-pyridinyl]oxy]-1-pyrrolidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】38836

【品名】tert-butyl (3R)-3-[[6-chloro-5-(4-cyanophenyl)-3-pyridinyl]oxy]-1-pyrrolidinecarboxylate

【CA登记号】

【分子式】C₂₁H₂₂ClN₃O₃

【分子量】399.8768

【元素组成】C 63.08% H 5.55% Cl 8.87% N 10.51% O 12%

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)

Mitsunobu coupling of N-Boc-3-(S)-hydroxypyrrolidine (I) with 3-bromo-2-chloro-5-hydroxypyridine (II) afforded ether (III). Subsequent introduction of the cyanophenyl group in (III) to give (V) was effected by Suzuki coupling with boronic acid (IV) in the presence of palladium catalyst. Finally, acid deprotection of the Boc group of (V) furnished the title compound.

参考文献中间体

合成目标

【1】 Shank, R.; Davis, C.; Reiltz, A.; Rivero, R.; Lee, J.; Discovery of novel pyridyl ethers as ligand for nicotinic acetylcholine receptor. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst MEDI 271.
【2】 Jung, S.L. (Ortho-McNeil Pharmaceutical, Inc.); Pyridyl ethers and thioethers as ligands for nicotinic acetylcholine receptor and its therapeutic application. WO 0010997 .

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)	16286	tert-butyl (3S)-3-hydroxytetrahydro-1H-pyrrole-1-carboxylate		C₉H₁₇NO₃	详情	详情
(II)	38833	5-bromo-6-chloro-3-pyridinol		C₅H₃BrClNO	详情	详情
(III)	38834	tert-butyl (3R)-3-[(5-bromo-6-chloro-3-pyridinyl)oxy]-1-pyrrolidinecarboxylate		C₁₄H₁₈BrClN₂O₃	详情	详情
(IV)	38835	4-cyanophenylboronic acid	126747-14-6	C₇H₆BNO₂	详情	详情
(V)	38836	tert-butyl (3R)-3-[[6-chloro-5-(4-cyanophenyl)-3-pyridinyl]oxy]-1-pyrrolidinecarboxylate		C₂₁H₂₂ClN₃O₃	详情	详情

Extended Information