3-(3-pyridinyl)-2-propyn-1-ol -Drug Synthesis Database

【结构式】

【分子编号】48612

【品名】3-(3-pyridinyl)-2-propyn-1-ol

【CA登记号】

【分子式】C₈H₇NO

【分子量】133.14972

【元素组成】C 72.17% H 5.3% N 10.52% O 12.02%

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：(III)

Palladium-catalyzed coupling of 3-bromopyridine (I) with propargyl alcohol (II) produced 3-(3-pyridyl)propargyl alcohol (III). Reaction of alcohol (III) with diketene (IV) in the presence of DMAP gave the acetoacetate ester (V), which was subsequently treated with ammonia in THF to furnish the enamino ester (VI). The title dihydropyridine derivative was then obtained by Hantzsch's synthesis upon condensation between ethyl 4-(2-isopropylimidazo[4,5-c]pyridin-1-yl)benzoylacetate (VII), enamino ester (VI) and 3,3-diphenylpropanal in refluxing EtOH.

参考文献中间体

合成目标

【1】 Tasaka, S.; Omori, H.; Tanabe, H.; Gomi, N.; Kiue, A. (Nikken Chemicals Co., Ltd.); 1,4-Dihydropyridine derivs.. EP 1055672; JP 2000044559; US 6306853; WO 9941250 .

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)	13255	methyl 3-[((1R,2E,4Z)-1-[(S)-hydroxy[3-(2-trityl-2H-1,2,3,4-tetraazol-5-yl)phenyl]methyl]-2,4-tetradecadienyl)sulfanyl]propanoate		C₄₅H₅₂N₄O₃S	详情	详情
(II)	16664	Propargyl Alcohol; 2-propyn-1-ol	107-19-7	C₃H₄O	详情	详情
(III)	48612	3-(3-pyridinyl)-2-propyn-1-ol		C₈H₇NO	详情	详情
(IV)	11367	4-Methylene-2-oxetanone; Acetyl ketene	674-82-8	C₄H₄O₂	详情	详情
(V)	48613	3-(3-pyridinyl)-2-propynyl 3-oxobutanoate		C₁₂H₁₁NO₃	详情	详情
(VI)	48614	3-(3-pyridinyl)-2-propynyl (E)-3-amino-2-butenoate		C₁₂H₁₂N₂O₂	详情	详情
(VII)	48615	ethyl 3-[4-(2-isopropyl-1H-imidazo[4,5-c]pyridin-1-yl)phenyl]-3-oxopropanoate		C₂₀H₂₁N₃O₃	详情	详情

Extended Information