93524-95-9 (3-(3-吡啶基)-2-丙烯-1-醇,3-(pyridin-4-yl)prop-2-yn-1-ol)

_96%

反应条件：

1.1 Reagents: Triethylamine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Triethylamine ; 16 h, rt

参考文献：

Photochemical synthesis and properties of axially chiral naphthylpyridines

Wessig, Pablo; Pick, Charlotte, Journal of Photochemistry and Photobiology, 2011, 222(1), 263-265

合成路线：1 步

626-61-9

_86%

反应条件：

1.1 Catalysts: Di-μ-chlorobis(η3-2-propenyl)dipalladium , rel-1,1′,1′′,1′′′-[(1R,2R,3S,4S)-1,2,3,4-Cyclopentanetetrayltetrakis(methylene)]… Solvents: Dimethylformamide ; 10 min, rt
1.2 Reagents: Potassium carbonate Catalysts: Cuprous iodide Solvents: Dimethylformamide ; 20 h, 100 °C

参考文献：

Sonogashira reaction of heteroaryl halides with alkynes catalyzed by a palladium-tetraphosphine complex

Feuerstein, Marie; Doucet, Henri; Santelli, Maurice, Journal of Molecular Catalysis A: Chemical, 2006, 256(1-2), 75-84

合成路线：1 步

7379-35-3

_86%

反应条件：

1.1 Reagents: Potassium carbonate Catalysts: Cuprous iodide , Di-μ-chlorobis(η3-2-propenyl)dipalladium , rel-1,1′,1′′,1′′′-[(1R,2R,3S,4S)-1,2,3,4-Cyclopentanetetrayltetrakis(methylene)]… Solvents: Dimethylformamide ; 20 h, 100 °C

参考文献：

Sonogashira cross-coupling reactions with heteroaryl halides in the presence of a tetraphosphine-palladium catalyst

Feuerstein, Marie; Doucet, Henri; Santelli, Maurice, Tetrahedron Letters, 2005, 46(10), 1717-1720

合成路线：1 步

2510-22-7

50-00-0

_84%

反应条件：

1.1 Reagents: 4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine Catalysts: Copper phenylacetylide Solvents: Benzene ; 5 min, rt; 30 min, 70 °C; 70 °C → rt
1.2 Solvents: Water ; 16 h, 70 °C

参考文献：

Copper-Catalysed Synthesis of Propargyl Alcohol and Derivatives from Acetylene and other Terminal Alkynes

Sitte, Nikolai A.; Ghiringhelli, Francesca; Shevchenko, Grigory A.; Rominger, Frank; Hashmi, A. Stephen K. ; et al, Advanced Synthesis & Catalysis, 2022, 364(13), 2227-2234

合成路线：1 步

_80%

反应条件：

1.1 Reagents: Triethylamine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium ; 60 °C

参考文献：

The insulin secretory action of novel polycyclic guanidines: Discovery through open innovation phenotypic screening, and exploration of structure-activity relationships

Shaghafi, Michael B.; Barrett, David G.; Willard, Francis S.; Overman, Larry E., Bioorganic & Medicinal Chemistry Letters, 2014, 24(4), 1031-1036

合成路线：1 步

_78%

反应条件：

1.1 Reagents: Triethylamine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium ; rt; 3 h, rt
1.2 Reagents: Ammonium chloride Solvents: Ethyl acetate , Water

参考文献：

Preparation of monoalkylpiperidines via the mild hydrogenation of monoalkynylpyridines

Usuki, Toyonobu ; Komatsu, Akira, Tetrahedron Letters, 2017, 58(29), 2856-2858

合成路线：1 步

_72%

反应条件：

1.1 Reagents: Triethylamine Catalysts: Triphenylphosphine , Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ; 4 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water

参考文献：

Preparation of heteroaryl-substituted pyrazolo[1,5-a]pyridines as RET inhibitors, pharmaceutical compositions and uses thereof

, World Intellectual Property Organization, , ,

合成路线：1 步

_57%

反应条件：

1.1 Reagents: Diisopropylethylamine Catalysts: Cuprous iodide , Tetrakis(triphenylphosphine)palladium ; 23 h, rt; 6 h, 70 °C

参考文献：

Palladium-catalyzed coupling reaction of halo heteroaromatic compounds in water

Inoue, Naoki; Sugimoto, Osamu; Tanji, Ken-ichi, Heterocycles, 2007, 72, 665-671

合成路线：1 步

74129-11-6

_32%

反应条件：

1.1 Reagents: Triethylamine Catalysts: Cuprous iodide , Tetrakis(triphenylphosphine)palladium Solvents: Chloroform ; 30 h, 50 °C

参考文献：

Preparation of β-amino acid derivatives as inhibitors of matrix metalloproteases and TNF-α

, United States, , ,

合成路线：1 步

反应条件：

1.1 Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ; 5 min, rt
1.2 Reagents: Triethylamine ; 16 h, rt

参考文献：

Chemoselective Hydrogenation of Alkynes to (Z)-Alkenes Using an Air-Stable Base Metal Catalyst

Zubar, Viktoriia; Sklyaruk, Jan; Brzozowska, Aleksandra; Rueping, Magnus, Organic Letters, 2020, 22(14), 5423-5428

合成路线：1 步

反应条件：

1.1 Reagents: Triethylamine Catalysts: Cuprous iodide , Dichlorobis(triphenylphosphine)palladium ; rt; 3 h, rt
1.2 Reagents: Ammonium chloride Solvents: Ethyl acetate

参考文献：

Method for the preparation of piperidine compound

, Japan, , ,

合成路线：1 步