Potassium Phosphate, Tribasic → 1006899-23-5

HRID 2356677Notes

Reaction equation

HRID 2356677 reaction equation
Cl[C:2]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[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.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[NH2:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([CH:11]2[CH2:13][CH2:12]2)[CH:9]=1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 887284-Amino-2-chlorobenzonitrileHCID 2760897Cyclopropylboronic acid

Product 1

HCID 593842271006899-23-5

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

269 mg of palladium acetate were added under an argon atmosphere to a suspension of 916 mg of 2-chloro-4-aminobenzonitrile, 773 mg of cyclopropylboronic acid, 5.094 g of potassium phosphate and 673 mg of tricyclohexylphosphine in a mixture of 10.5 ml of toluene and 1.74 ml of water. The mixture was stirred at 80° C. overnight. The cooled reaction mixture was admixed with water and ethyl acetate and filtered, and the filtrate was extracted three times with a mixture of ethyl acetate with toluene. The organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography (method [PR1]) and afforded 4-amino-2-cyclopropylbenzonitrile. 1H NMR: 7.3, d, 1H; 6.4, d, 1H, 6.1, d, 1H, 4.0, s (broad), 2H, 2.0, m, 1H, 1.0, m, 2H, 0.65, m, 2H.

Workup

  1. customThe cooled reaction mixture
  2. filtrationfiltered
  3. extractionthe filtrate was extracted three times
  4. additionwith a mixture of ethyl acetate with toluene
  5. dry with materialThe organic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography (method [PR1])

Sources & evidence

ORD record
ord-8d4a0da79dfb4c9a8e5a57361cbc3ae6
Source dataset
uspto-grants-2010_07
Patent number
US07759366B2

Reaction notes

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