Potassium Carbonate → HCID 23434230, compound

HRID 1015420Notes

Reaction equation

HRID 1015420 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[NH2:14][C:15]1[CH:22]=[CH:21][C:20](Br)=[CH:19][C:16]=1[C:17]#[N:18].C(=O)([O-])[O-].[K+].[K+]>O.COCCOC>[NH2:14][C:15]1[CH:22]=[CH:21][C:20]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=2)=[CH:19][C:16]=1[C:17]#[N:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 4297402-Amino-5-bromobenzonitrileHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 23434230HCID 23434230, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

In 250 ml of water and 500 ml of 1,2-dimethoxyethane, was mixed 26.5 g of 4-(trifluoromethyl)benzeneboronic acid, 25 g of 2-amino-5-bromo-benzonitrile and 57.9 g of potassium carbonate. The mixture was bobbled through with nitrogen for 10 minutes, then 1 g of bis(triphenylphosphine)palladium(II) choride was added and the reaction mixture was heated at reflux overnight. The reaction mixture was cooled to room temperature, added 700 ml of water and extracted with 800 ml of ethyl acetate. The organic phase was washed first with 300 ml of saturated sodium chloride, then 300 ml of 2 M calcium chloride and at last with 300 ml of water. The organic phase was dried with magnesium sulfate, evaporated to an oil and trituated with ether. Yield 30.5 g (92%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. extractionextracted with 800 ml of ethyl acetate
  4. washThe organic phase was washed first with 300 ml of saturated sodium chloride
  5. dry with materialThe organic phase was dried with magnesium sulfate
  6. customevaporated to an oil

Sources & evidence

ORD record
ord-43af7ca75b49429b875d7091ad7b5466
Source dataset
uspto-grants-2011_07
Patent number
US07985761B2

Reaction notes

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