Potassium Carbonate → HCID 67994323, compound

HRID 1186719Notes

Reaction equation

HRID 1186719 reaction equation
O([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[N+:19]([O-:21])=[O:20])S(C(F)(F)F)(=O)=O.[NH2:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[C:26]#[N:27].C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[N+:19]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][C:9]=1[NH:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[C:26]#[N:27])([O-:21])=[O:20]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 167023-AminobenzonitrileHCID 147652731-Nitronaphthalen-2-yl triflate

Product 1

HCID 67994323HCID 67994323, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

An anhydrous toluene (40 mL) suspension of 1-nitronaphthalen-2-yl triflate (3.00 g, 8.64 mmol), 3-aminobenzonitrile (1.02 g, 8.64 mmol), potassium carbonate (1.19 g, 8.64 mmol), triphenylphosphine (227 mg, 0.864 mmol), and tetrakis(triphenylphosphine)palladium (500 mg, 0.432 mmol) was stirred at 110° C. for 18 hours. After cooling on standing, the reaction mixture was filtered, and the filtrate was diluted with ethyl acetate. The obtained organic solution was washed with a saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=99/1) to obtain the titled compound as a yellow powder (1.60 g, yield 64%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. additionthe filtrate was diluted with ethyl acetate
  4. washThe obtained organic solution was washed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed by evaporation under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform/methanol=99/1)

Sources & evidence

ORD record
ord-a1119e85835a4b329de25ff3a5d5493b
Source dataset
uspto-grants-2014_03
Patent number
US08673915B2

Reaction notes

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