Triethylamine → HCID 22503325, compound

HRID 1814484Notes

Reaction equation

HRID 1814484 reaction equation
Br[C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)#[CH:11].C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>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.C(OCC)(=O)C.N1C=CC=CC=1>[C:8]([C:3]1[C:2]([C:11]#[C:10][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:9]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 2510201-Ethynyl-4-methoxybenzeneHCID 8176943-Bromopyridine-2-carbonitrile

Product 1

HCID 22503325HCID 22503325, compoundYield 81%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-bromo-2-cyanopyridine (3.63 g, 19.8 mmol), 4-ethynylanisole (3.15 g, 1.2 equivalents), dichlorobis(triphenylphosphine)palladium (II) (0.28 g, 0.02 equivalent), copper (I) iodide (0.14 g), triethylamine (60 ml) and dry pyridine (6 ml) was heated under reflux in nitrogen atmosphere for 12.5 hr. After the mixture was cooled as it was, ethyl acetate and a 10% aqueous solution of sodium carbonate were added thereto. The resulting mixture was stirred, and the resulting insoluble matters were filtered off. The organic layer was separated and washed with water/brine (1:1(v/v)) and brine in this order, and then dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate/chloroform/methanol system). The resulting product was recrystallized from chloroform/n-hexane, to give the title compound as a pale yellow powder (3.53 g, yield; 81%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in nitrogen atmosphere for 12.5 hr
  3. temperatureAfter the mixture was cooled as it
  4. filtrationthe resulting insoluble matters were filtered off
  5. customThe organic layer was separated
  6. washwashed with water/brine (1:1(v/v)) and brine in this order
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate/chloroform/methanol system)
  10. customThe resulting product was recrystallized from chloroform/n-hexane

Sources & evidence

ORD record
ord-f677070b7cd54df1af641a040a4e90b3
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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