Potassium Phosphate, Tribasic → N-(2-Cyclopropyl-4-fluorophenyl)acetamide

HRID 1478808Notes

Reaction equation

HRID 1478808 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:12])[CH3:11].[CH:13]1(B(O)O)[CH2:15][CH2:14]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O.C1(C)C=CC=CC=1>[CH:13]1([C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=2[NH:9][C:10](=[O:12])[CH3:11])[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 688184N-(2-bromo-4-fluorophenyl)acetamideHCID 2760897Cyclopropylboronic acid

Product 1

HCID 118513265N-(2-Cyclopropyl-4-fluorophenyl)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture comprising N-(2-bromo-4-fluorophenyl)acetamide (1 g, 4.31 mmol), cyclopropylboronic acid (0.481 g, 5.60 mmol), tricyclohexylphosphine (0.121 g, 0.431 mmol), potassium phosphate (tribasic) (3.20 g, 15.08 mmol), toluene (10 ml) and water (10 ml) was equally divided between two 10-20 ml microwave tubes. Each reaction tube was sealed, evacuated and filled with nitrogen (3×) and placed in the microwave at 100° C. for 6 hrs. The contents of the vials were combined, diluted with EtOAc and the layers separated. The organic extracts were washed with water (2×), dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound as a brown solid. The product was used crude in the next step.

Workup

  1. customEach reaction tube was sealed
  2. customevacuated
  3. additionfilled with nitrogen (3×)
  4. additiondiluted with EtOAc
  5. customthe layers separated
  6. washThe organic extracts were washed with water (2×)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-603e45abb7954628915760b23c06aa9c
Source dataset
uspto-grants-2016_08
Patent number
US09403833B2

Reaction notes

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