Cyclopropylacetylene → HCID 57804191, compound

HRID 2102908Notes

Reaction equation

HRID 2102908 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[C:14]([CH:16]1[CH2:18][CH2:17]1)#[CH:15]>C1(C)C=CC=CC=1.C(N(CC)CC)C.[Cu]I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=[C:4]([C:15]#[C:14][CH:16]2[CH2:18][CH2:17]2)[N:3]=1

Participants

7

Reactant 2

HCID 138823CyclopropylacetyleneHCID 12263987Ethyl 2,6-dichloronicotinate

Product 1

HCID 57804191HCID 57804191, compoundYield 31%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

Ethyl 2,6-dichloropyridine-3-carboxylate (2.0 g, 9.1 mmol), ethynylcyclopropane (1.6 mL of a 70% w/v solution in toluene, 13.63 mmol), copper(I) iodide (173 mg, 0.9 mmol), bis(triphenylphosphine) palladium(II) chloride (1.28 g, 1.82 mmol) were stirred in 40 mL triethylamine at room temperature for 24 h. The solvent was removed in vacuo and the residue was purified by column chromatography using 10-50% EtOAc/hexane to give the product (0.7 g, 31%) as a brown oil. m/z=250 (M+1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8c2e775bf19849fdaac9bf2e355dc5f4
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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