Cyclopropylacetylene → Ethyl 5-cyclopropylethynyl-pyridine-2-carboxylate

HRID 1842226Notes

Reaction equation

HRID 1842226 reaction equation
[CH:1]1([C:4]#[CH:5])[CH2:3][CH2:2]1.Br[C:7]1[CH:8]=[CH:9][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:11][CH:12]=1>C(NC(C)C)(C)C.[Cu](I)I>[CH:1]1([C:4]#[C:5][C:7]2[CH:8]=[CH:9][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:11][CH:12]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 138823CyclopropylacetyleneHCID 12686158Ethyl 5-bromopicolinate

Product 1

HCID 57827602Ethyl 5-cyclopropylethynyl-pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 7912DiisopropylamineSolvent

Procedure

Cyclopropylacetylene (73.7 μL), copper iodide (3.16 mg) and tetrakis (triphenylphosphine)palladium (9.59 mg) were added to a solution of ethyl 5-bromopyridine-2-carboxylate (95.5 mg) in diisopropylamine (2 mL) at room temperature, and the mixture was stirred at room temperature for 17 hours and five minutes. The reaction solution was concentrated under reduced pressure. The residue was purified by NH-silica gel column chromatography to obtain the title compound (19.4 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThe residue was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-e9fdaf9d6f9b4700ba0bda423671ba12
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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