Triethylamine → 5-(3-Trifluoromethoxyphenylethynyl)-nicotinonitrile

HRID 606902Notes

Reaction equation

HRID 606902 reaction equation
C(N(CC)CC)C.Br[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH:16]=1)[C:14]#[N:15].[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=1)#[CH:18]>C(OCC)(=O)C.[Cu]I.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:27][C:26]([F:28])([F:29])[O:25][C:21]1[CH:20]=[C:19]([C:17]#[C:18][C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH:16]=2)[C:14]#[N:15])[CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 7367935-BromonicotinonitrileHCID 269862623-(Trifluoromethoxy)Phenylacetylene

Product 1

HCID 670475485-(3-Trifluoromethoxyphenylethynyl)-nicotinonitrileYield 15%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Add triethylamine (1.73 mL, 12.28 mmol), copper (I) iodide (34.0 mg, 0.180 mmol) and bis(triphenylphosphine)palladium (II) dichloride (107.7 mg, 0.150 mmol) to a solution of 5-bromonicotinonitrile (562.2 mg, 3.07 mmol) and 1-ethynyl -3-trifluoromethoxybenzene, (prepared as described in PREPARATION 28), (571.4 mg, 3.07 mmol) in ethyl acetate (3 mL). Stir in a sealed tube at 50° C. for 18 h, concentrate and purify the residue by silica gel chromatography, eluting with 100:0 to 100:50 hexanes:ethyl acetate, to give the title compound (130 mg, 15%).

Workup

  1. concentrationconcentrate
  2. custompurify the residue by silica gel chromatography
  3. washeluting with 100:0 to 100:50 hexanes

Sources & evidence

ORD record
ord-8576a567435041f0bfa9ddb0cce0e1b0
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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