Triethylamine → HCID 86679096, compound

HRID 1183488Notes

Reaction equation

HRID 1183488 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[CH:9]1([C:14]#[CH:15])[CH2:13][CH2:12][CH2:11][CH2:10]1.C(N(CC)CC)C>CN(C=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:15]#[C:14][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 122742,6-DibromopyridineHCID 136725Cyclopentylacetylene

Product 1

HCID 86679096HCID 86679096, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

2,6-Dibromo-pyridine (0.544 g, 2.34 mmol), cyclopentylacetylene (0.220 g, 2.34 mmol), copper(I) iodide (0.445 g, 2.34 mmol), triethylamine (0.98 mL, 7.01 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.164 g, 0.023 mmol) were combined in DMF and stirred at room temperature for 2 days. The reaction was purified via silica gel chromatography to afford the title compound.

Workup

  1. customThe reaction was purified via silica gel chromatography

Sources & evidence

ORD record
ord-3b31c7222da2400689f4d3f1d8d1eab4
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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