Potassium Carbonate → N-(3'-Amino-3,5-dimethyl-biphenyl-2-yl)-2-(4-fluoro-phenyl)-acetamide

HRID 1820146Notes

Reaction equation

HRID 1820146 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH:10][C:11](=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1.[NH2:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:21][C:22]1[CH:27]=[C:26]([C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=2[NH:10][C:11](=[O:20])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 922693-Aminophenylboronic acidHCID 11530121N-(2-Bromo-4,6-dimethyl-phenyl)-2-(4-fluoro-phenyl)-acetamide

Product 1

HCID 11681788N-(3'-Amino-3,5-dimethyl-biphenyl-2-yl)-2-(4-fluoro-phenyl)-acetamideYield 95.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 180AcetoneSolvent

Conditions

Temperature
125 °C

Procedure

N-(2-Bromo-4,6-dimethyl-phenyl)-2-(4-fluoro-phenyl)-acetamide (1c, 15.1 mg), 3-aminobenzeneboronic acid (30.8 mg), aqueous potassium carbonate (5 M, 90 uL) and palladium(II) acetate (1 mg) were mixed in acetone (2 mL) and heated to 125° C. for 15 minutes in a sealed microwave process vial. The reaction mixture was filtered through silica (500 mg), concentrated in vacuo, redissolved in dimethyl sulfoxide (0.5 mL) and subjected to preparative LC-MS purification to furnish 14.9 mg (95% yield) of the title compound as an oil. LC-MS (m/z) 349 (MH+); tR=1.92, (UV, ELSD) 98%, 99%.

Workup

  1. filtrationThe reaction mixture was filtered through silica (500 mg)
  2. concentrationconcentrated in vacuo
  3. dissolutionredissolved in dimethyl sulfoxide (0.5 mL)
  4. customsubjected to preparative LC-MS purification

Sources & evidence

ORD record
ord-b2804430fa0548ebaca5fd93c12a5ad5
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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