Potassium Phosphate, Tribasic → HCID 66899536, compound

HRID 571957Notes

Reaction equation

HRID 571957 reaction equation
[NH2:1][C:2]1[C:9](Br)=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1Br.[CH:12]1(B(O)O)[CH2:14][CH2:13]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P([CH:39]2[CH2:44][CH2:43]CCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:1][C:2]1[C:9]([CH:12]2[CH2:14][CH2:13]2)=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH:43]1[CH2:44][CH2:39]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27353144-amino-3,5-dibromobenzonitrileHCID 2760897Cyclopropylboronic acid

Product 1

HCID 66899536HCID 66899536, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Palladium (II) acetate (814 mg, 3.62 mmol) was added to a stirred mixture of 4-amino-3,5-dibromobenzonitrile (5.00 g, 18.1 mmol), cyclopropanboronic acid (3.89 g, 45.3 mmol), potassium phosphate tribasic (23.1 g, 109 mmol) and tricyclohexylphosphine (1.02 g, 3.62 mmol) in toluene (20.0 mL) and water (1.0 mL). The resulting mixture was degassed and heated to 100° C. After 3 h, the reaction mixture was cooled to rt, diluted with water and extracted with EtOAc. The organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (gradient elution, 0-15% EtOAc/hexanes as eluent) to afford the title compound i-7a. m/z (ES) 199 (MH)+.

Workup

  1. customThe resulting mixture was degassed
  2. temperaturethe reaction mixture was cooled to rt
  3. additiondiluted with water
  4. extractionextracted with EtOAc
  5. washThe organics were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by column chromatography on silica gel (gradient elution, 0-15% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-d4654b29fac44e449bb6c6ee0d85e9cb
Source dataset
uspto-grants-2015_05
Patent number
US09029377B2

Reaction notes

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