Triethylamine → 5-(3,4-Dimethylphenylethynyl)-nicotinonitrile

HRID 606838

Reaction equation

HRID 606838 reaction equation
I[C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([CH3:8])=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:17]([C:19]1[CH:20]=[N:21][CH:22]=[C:23]([CH:26]=1)[C:24]#[N:25])#[CH:18]>C(#N)C.C(OCC)C.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.[Cu]I>[CH3:9][C:4]1[CH:3]=[C:2]([C:18]#[C:17][C:19]2[CH:20]=[N:21][CH:22]=[C:23]([CH:26]=2)[C:24]#[N:25])[CH:7]=[CH:6][C:5]=1[CH3:8]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 1416464-Iodo-1,2-dimethylbenzeneHCID 224165635-Ethynylnicotinonitrile

Product 1

HCID 670475425-(3,4-Dimethylphenylethynyl)-nicotinonitrileYield 62%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

Combine 4-iodo-o-xylene (0.362 g, 1.561 mmol), bis(triphenylphosphine)palladium (II) dichloride (55 mg, 0.078 mmol), and copper (I) iodide (30 mg, 0.156 mmol) in triethylamine (0.653 mL, 4.683 mmol) and stir under nitrogen for 5 min at 80° C. Add a solution of 5-ethynylnicotinonitrile, (prepared essentially as described in PREPARATION 4), (200 mg, 1.561 mmol) in anhydrous acetonitrile (2.50 mL), and stir under nitrogen overnight. Cool to room temperature and dilute with diethyl ether. Wash with a saturated aqueous solution of sodium bicarbonate, dry (sodium sulfate), filter, and concentrate. Purify the residue by silica gel chromatography, eluting with 95:5 to 50:50 dichloromethane:ethyl acetate, to give the title compound as a yellow solid (225 mg, 62%).

Workup

  1. custom(prepared essentially
  2. washWash with a saturated aqueous solution of sodium bicarbonate
  3. dry with materialdry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the residue by silica gel chromatography
  7. washeluting with 95:5 to 50:50 dichloromethane

Sources & evidence

ORD record
ord-f070616815b445c8816ea82e3b9c3f6a
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Linked notes

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