Potassium Carbonate → HCID 23497808, compound

HRID 1837144Notes

Reaction equation

HRID 1837144 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:15]=[CH:16][CH:17]=2)=O)[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[C:13]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:10][NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 976228HCID 976228, compound

Product 1

HCID 23497808HCID 23497808, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of borane-dimethylsulfide complex (2.0 M, 9 mL, 18 mmol) was added to a solution of biphenyl-2-carboxylic acid (3-methoxy-phenyl)-amide (3.03 g 10 mmol) in toluene (10 mL). The reaction mixture was refluxed and stirred for 42 hours. The reaction mixture was cooled to room temperature, 10% aqueous potassium carbonate (10 mL) was added, and the reaction mixture was vigorously stirred for 30 minutes. Extraction of the aqueous layer with ethyl acetate followed by concentration gave the crude product. Purification by silica gel column chromatography using 20% ethyl acetate in hexanes as the eluant afforded the pure product (1.4 g). MH+290: 1H (CDCl3) δ 3.72 (3H, s), 4.23 (2H, s), 6.07 (1H, m), 6.14 (1H, dm, J=8), 6.25 (1H, dm, J=8), 7.03 (1H, t, J=8), 7.22-7.32 (8H, m), 7.52 (1H, m).

Workup

  1. temperatureThe reaction mixture was refluxed
  2. stirringthe reaction mixture was vigorously stirred for 30 minutes
  3. extractionExtraction of the aqueous layer with ethyl acetate
  4. concentrationfollowed by concentration
  5. customgave the crude product
  6. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-123f62b49517497cbee0d257874200d6
Source dataset
uspto-grants-2004_08
Patent number
US06780883B2

Reaction notes

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