Cyclopropylacetylene → HCID 57827602, compound

HRID 1693194Notes

Reaction equation

HRID 1693194 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.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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

6

Reactant 2

HCID 138823CyclopropylacetyleneHCID 12686158Ethyl 5-bromopicolinate

Product 1

HCID 57827602HCID 57827602, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 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-c482ae25450240a28c49dde6a0290a48
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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