Triphenylphosphine → HCID 57987435, compound

HRID 1869750Notes

Reaction equation

HRID 1869750 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7](Cl)[CH:6]=1.[C:13]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)#[CH:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])(O)=O.[Na+]>CCN(CC)CC.O1CCOCC1.[Cu]I.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:14]#[C:13][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][CH:16]=2)[CH:6]=1

Participants

9

Reactant 4

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 43482951-Ethynyl-4-(trifluoromethyl)benzeneHCID 24729490Methyl (2-chloropyridin-4-yl)acetate

Product 1

HCID 57987435HCID 57987435, compoundYield 17.3%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of methyl(2-chloropyridin-4-yl)acetate (1 g, 5.4 mmol), 1-ethynyl-4-(trifluoromethyl)benzene (3.6 ml, 22 mmol), triphenylphosphine (141 mg, 0.54 mmol), CuI (105 mg, 0.54 mmol), and tetrakis(triphenylphosphine) palladium (0) (312 mg, 0.54 mmol) in Et3N (5 ml) and dioxane (5 ml) in a sealed microwave vial was heated, under microwave irradiation at 150° C. for 15 minutes. The reaction was treated with NaHCO3 (half saturated and extracted with EtOAc (×2). The extracts were washed with brine dried (MgSO4) and evaporated in vacuo to a brown gum which was purified by chromatography (silica, 25% EtOAc/isohexane) to give the acetylene (298 mg, 17%). M/Z (ES+) 320 (MH+).

Workup

  1. extractionextracted with EtOAc (×2)
  2. washThe extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo to a brown gum which
  5. customwas purified by chromatography (silica, 25% EtOAc/isohexane)

Sources & evidence

ORD record
ord-3b248a5263be43ee98f3864a66454819
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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