Triethylamine → HCID 22503325, compound

HRID 1006921Notes

Reaction equation

HRID 1006921 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-598d194de4414bf187382cf2c7f4edb6
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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