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183438-97-3

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Basic Information

Molecular Structure:
CAS No.:	183438-97-3
Name:	2-Pyridinecarboxaldehyde, 6-ethynyl- (9CI)
Article Data:	4

Formula:	C8H5 N O
Molecular Weight:	131.134
Synonyms:	6-Ethynylpyridine-2-carboxaldehyde
Density:	1.15±0.1 g/cm3(Predicted)
Boiling Point:	237.1±25.0 °C(Predicted)
PSA:	29.96000
LogP:	0.87540

Synthetic route

: 183438-94-0
6-(2-trimethylsilylethynyl)pyridin-2-carbaldehyde

: 183438-97-3
6-ethynylpyridine-2-carboxaldehyde

Conditions	Yield
With potassium carbonate	98%
With potassium carbonate	98%
With methanol; potassium carbonate at 20℃; for 1h;	83.4%
With potassium carbonate In methanol at 20℃; for 1h; Inert atmosphere;	83.4%

: 626-05-1
2,6-Dibromopyridine

: 183438-97-3
6-ethynylpyridine-2-carboxaldehyde

Conditions	Yield
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane 1.2: 78 percent / tetrahydrofuran; hexane 2.1: 95 percent / copper(I) iodide / tetrakis(triphenylphosphine)palladium(0) 3.1: 98 percent / potassium carbonate View Scheme
Multi-step reaction with 3 steps 1.1: BuLi / tetrahydrofuran; hexane 1.2: tetrahydrofuran; hexane 1.3: 78 percent / HCl / tetrahydrofuran; hexane 2.1: 95 percent / Pd(PPh3)4; CuI 3.1: 98 percent / K2CO3 View Scheme

: 34160-40-2
6-bromo-2-pyridinecarbaldehyde

: 183438-97-3
6-ethynylpyridine-2-carboxaldehyde

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / copper(I) iodide / tetrakis(triphenylphosphine)palladium(0) 2: 98 percent / potassium carbonate View Scheme
Multi-step reaction with 2 steps 1: 95 percent / Pd(PPh3)4; CuI 2: 98 percent / K2CO3 View Scheme
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / 20 °C / Inert atmosphere 2: potassium carbonate; methanol / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; triethylamine / 20 °C / Inert atmosphere 2: potassium carbonate / methanol / 1 h / 20 °C / Inert atmosphere View Scheme

: 762262-22-6
2-bromo-6-(4-hexyl-phenylethynyl)-pyridine

: 183438-97-3
6-ethynylpyridine-2-carboxaldehyde

: 804555-76-8
2-formyl-6-[6-(4-hexylphenylethynyl)pyridin-2-ylethynyl]pyridine

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) Sonogashira coupling;	74%
With copper(l) iodide; diisopropylamine; tetrakis(triphenylphosphine) palladium(0) In toluene at 40℃; for 12h; Sonogashira coupling;	74%

: 286947-68-0
pentafluoro(4-iodophenyl)-λ6-sulfane

: 183438-97-3
6-ethynylpyridine-2-carboxaldehyde

: 1401165-57-8
6-((4-(pentafluorothio)phenyl)ethynyl)picolinaldehyde

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In acetonitrile at 20 - 80℃; for 0.5h;	57%

: 4-(6-(3,6-diazabicyclo[3.1.1]heptan-3-yl)pyridin-3-yl)-6-(1-methyl-1H-pyrazol-4-yl)pyrazole[1,5-a]pyridine-3-carbonitrile dihydrochloride

: 183438-97-3
6-ethynylpyridine-2-carboxaldehyde

: 4-(6-(6-((6-ethynylpyridin-2-yl)methyl)-3,6-diazabicyclo[3.1.1]hept-3-yl)pyridin-3-yl)-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile

Conditions	Yield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 35℃;	48.93%

: 183438-97-3
6-ethynylpyridine-2-carboxaldehyde

: C92H66N4

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 74 percent / Pd(PPh3)4; CuI 2.1: BuLi / tetrahydrofuran; hexane / 2 h / -78 °C 2.2: ClP(O)(OEt)2 / tetrahydrofuran; hexane / 2 h / 20 °C 2.3: 53 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 2 h / -78 - 20 °C View Scheme

: 286947-68-0
pentafluoro(4-iodophenyl)-λ6-sulfane

: 183438-97-3
6-ethynylpyridine-2-carboxaldehyde

: (2R)-3-methyl-2-{[(6-{[4-(pentafluoro-λ6-sulfanyl)phenyl]ethynyl}pyridin-2-yl)methyl]amino}butan-1-ol

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / acetonitrile / 0.5 h / 20 - 80 °C 2: acetic acid / MP-cyanoborohydride / dichloromethane; methanol / 20 °C View Scheme

: 50-00-0
formaldehyd

: 2198-58-5, 16713-15-8, 84609-46-1
N,N-diethyl-1,4-phenylenediamine dihydrochloride

: 183438-97-3
6-ethynylpyridine-2-carboxaldehyde

: 2-(4-(diethylamino)phenyl)-5-ethynyl-2H-imidazo[1,5-a]pyridin-4-ium chloride

Conditions	Yield
In ethanol at 20 - 25℃;

: 4-(6-(3,6-diazabicyclo[3.1.1]heptan-3-yl)pyridin-3-yl)-6-(2-hydroxy-2-methylpropoxy)pyrazolo[1,5-a]pyridine-3-carbonitrile dihydrochloride

: 183438-97-3
6-ethynylpyridine-2-carboxaldehyde

: 4-(6-(6-((6-ethynylpyridin-2-yl)methyl)-3,6-diazabicyclo[3.1.1]heptan-3-yl)pyridin-3-yl)-6-(2-hydroxy-2-methylpropoxy)pyrazolo[1,5-a]pyridine-3-carbonitrile

Conditions	Yield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 35℃; Inert atmosphere;

Raw Materials

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