Potassium Carbonate → N-{3-[2-(2,4-Dichloro-benzoyl)-3-trifluoromethyl-benzofuran-6-yl]-phenyl}-acetamide

HRID 29245

Reaction equation

HRID 29245 reaction equation
[Cl:1][C:2]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:3]=1[C:4]([C:6]1[O:7][C:8]2[CH:18]=[C:17](OS(C(F)(F)F)(=O)=O)[CH:16]=[CH:15][C:9]=2[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5].[C:32]([NH:35][C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=1)(=[O:34])[CH3:33].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:3]=1[C:4]([C:6]1[O:7][C:8]2[CH:18]=[C:17]([C:40]3[CH:41]=[C:36]([NH:35][C:32](=[O:34])[CH3:33])[CH:37]=[CH:38][CH:39]=3)[CH:16]=[CH:15][C:9]=2[C:10]=1[C:11]([F:12])([F:13])[F:14])=[O:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 157274(3-Acetamidophenyl)boronic acidHCID 59788897Trifluoro-methanesulfonic acid 2-(2,4-dichloro-benzoyl)-3-trifluoromethyl-benzofuran-6-yl ester

Product 1

HCID 59788917N-{3-[2-(2,4-Dichloro-benzoyl)-3-trifluoromethyl-benzofuran-6-yl]-phenyl}-acetamideYield 18.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of trifluoro-methanesulfo4nic acid 2-(2,4-dichloro-benzoyl)-3-trifluoromethyl-benzofuran-6-yl ester from step 2 (110 mg, 0.217 mmol) in anhydrous N,N-dimethylformamide (2 mL) were added 3-acetamidobenzene boronic acid (58.2 mg, 0.325 mmol, 1.5 eq), potassium carbonate (60.0 mg, 0.434 mmol, 2 eq) and tetrakis(triphenylphosphine)palladium(0) (50 mg, 0.043 mmol, 0.2 eq) under argon. The resulting reaction mixture was degassed for 5 min. and then the reaction was then stirred at 80° C. for 6 h. The mixture was cooled to room temperature then poured into ethyl acetate (10 mL) and water (10 mL). The aqueous layer was extracted with ethyl acetate (2×10 mL), and the combined organic layers were washed with water (2×10 mL), dried over Na2SO4, filtrated, and evaporated in vacuo. The residue was purified by pre-HPLC to afford an yellow solid (19.5 mg, 18.3%) as product. 1H-NMR (DMSO-d6): 10.08 (s, 1H), 8.10 to 7.99 (m, 3H), 7.91 (d, J=2.0 Hz, 1H), 7.88 (d, J=8.5 Hz, 1H), 7.81 (dd, J=8.5, 1.7 Hz, 1H), 7.70 (dd, J=8.4, 2.3 Hz, 1H), 7.59 (dt, J=7.6, 2.0 Hz, 1H), 7.47 to 7.37 (m, 2H), 2.06 (s, 3H); LC-MS (MH+=492/494).

Workup

  1. customThe resulting reaction mixture
  2. customwas degassed for 5 min.
  3. temperatureThe mixture was cooled to room temperature
  4. additionthen poured into ethyl acetate (10 mL) and water (10 mL)
  5. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
  6. washthe combined organic layers were washed with water (2×10 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltrated
  9. customevaporated in vacuo
  10. customThe residue was purified by pre-HPLC

Sources & evidence

ORD record
ord-2bce659dbbcc4a19b80b443f8a894767
Source dataset
uspto-grants-2008_09
Patent number
US07420066B2

Linked notes

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