Potassium Carbonate → HCID 66654425, compound
Reaction equation
[NH2:1][C:2]1[C:9](I)=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[C:15](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.CCOC(C)=O.O.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>[NH2:1][C:2]1[C:9]([CH3:15])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 4-amino-5-iodo-2-(trifluoromethyl)benzonitrile (commercially available, for example from Key Organics Ltd., Camelford, UK, 640 mg, 2.05 mmol) and potassium carbonate (567 mg, 4.10 mmol) in 1,4-Dioxane (10 ml) was added tetrakis(triphenylphosphine)palladium(0) (237 mg, 0.205 mmol) and trimethylboroxin (1.43 ml, 10.3 mmol) under argon atmosphere. The reaction mixture was heated to 100° C. overnight. The reaction mixture was diluted in EtOAc (100 ml) and water (50 ml). The aqueous was extracted with EtOAc (100 ml). The organics were combined, passed through a phase separator and concentrated to afford 1 g of a yellow oil which was purified by flash chromatography using a Biotage SP4 (eluting a gradient from 30% to 70% EtOAc in hexane). Relevant fractions were combined and concentrated to afford 300 mg of the title compound as a yellow solid.
Workup
- extractionThe aqueous was extracted with EtOAc (100 ml)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-42d26ffa882c47b6a778b5779b7985cb
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115132B2
Reaction notes
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