Triethylamine → HCID 57656230, compound

HRID 911755Notes

Reaction equation

HRID 911755 reaction equation
[CH:1]1([C:7]#[CH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][N:18]=1>CN(C=O)C.CCCCCC.CCOC(C)=O.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.[Cu](I)I>[CH:1]1([C:7]#[C:8][C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][N:18]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 70263EthynylcyclohexaneHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 57656230HCID 57656230, compoundYield 84.1%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
100 °C

Procedure

Add cyclohexylacetylene (1.54 mL, 11.6 mmol), dichlorobis(triphenylphosphine)palladium (200 mg, 0.28 mmol), copper iodide (100 mg, 0.53 mmol), and triethylamine (2.0 mL, 14.3 mmol) to a solution of 6-chloronicotinonitrile (1.38 g, 9.9 mmol) in DMF (4 mL). Heat the mixture in a sealed flask for 3 h at 100° C. Cool the mixture to room temperature, dilute with 1:1 hexane/EtOAc (100 mL) and wash with an aqueous 10% sodium chloride solution (3×30 mL). Collect the organic layer, concentrate in vacuo, and purify the residue by silica gel chromatography (90 g silica, hexane/EtOAc 95/5 to 85/15 gradient) to obtain the desired intermediate (1.75 g, 83%)

Workup

  1. temperatureCool the mixture to room temperature
  2. washwash with an aqueous 10% sodium chloride solution (3×30 mL)
  3. customCollect the organic layer
  4. concentrationconcentrate in vacuo
  5. custompurify the residue by silica gel chromatography (90 g silica, hexane/EtOAc 95/5 to 85/15 gradient)

Sources & evidence

ORD record
ord-59ce7acb335d4315a28f5c399dc5d5b7
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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