Potassium Phosphate, Tribasic → 4-Amino-3-cyclopropylbenzonitrile
Reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1I.[CH:11]1(B(O)O)[CH2:13][CH2:12]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH:11]1[CH2:13][CH2:12]1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
Palladium (II) acetate (798 mg, 3.55 mmol) was added to a stirred mixture of 4-amino-3-iodobenzonitrile (5.08 g, 20.8 mmol), cyclopropyl boronic acid (2.69 g, 31.3 mmol), potassium phosphate (22.9 g, 108 mmol) and tricyclohexylphosphine (1.17 g, 4.17 mmol) in toluene (40 mL)/water (2 mL). The reaction mixture was degassed and heated to 100° C. for 3 h. After cooling to rt, the reaction mixture was poured into water and extracted with EtOAc. The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (gradient elution; 0-20% EtOAc/hexanes as eluent) to afford the title compound i-4-a. m/z (ES) 159 (MH)+
Workup
- customThe reaction mixture was degassed
- temperatureAfter cooling to rt
- additionthe reaction mixture was poured into water
- extractionextracted with EtOAc
- washThe combined organics were washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe crude residue was purified by column chromatography on silica gel (gradient elution; 0-20% EtOAc/hexanes as eluent)
Sources & evidence
- ORD record
- ord-b302ff4497ec45f3ab94958ad09c7055
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029377B2
Reaction notes
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