Potassium Carbonate → HCID 58130366, compound

HRID 1515367Notes

Reaction equation

HRID 1515367 reaction equation
I[C:2]1[C:11](=[O:12])[C:10]2[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[CH:7]=[CH:6][C:5]=2[S:4][C:3]=1[CH3:17].[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.[Pd].ClP(Cl)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:17][C:3]1[S:4][C:5]2[CH:6]=[CH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10]=2[C:11](=[O:12])[C:2]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 58130401HCID 58130401, compound

Product 1

HCID 58130366HCID 58130366, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 60079406HCID 60079406, compoundCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

The compound (1.0 mmol, 352 mg) obtained in (1) above, dichloro triphenylphosphine palladium (0.03 mmol, 21 mg), phenylboronic acid (1.3 mmol, 159 mg) and potassium carbonate (4.0 mmol, 552 mg) were dissolved in degassed dimethylformamide (3.2 mL) and water (0.8 mL), and the resulting solution was stirred under a nitrogen atmosphere at 80° C. for 4 hours. After the disappearance of the starting materials was confirmed by thin-layer chromatography, water was poured into the reaction solution to terminate the reaction. The organic substances were extracted with ethyl acetate, the obtained organic layer was dried over magnesium sulfate, and the solvents were evaporated under reduced pressure. The residue was purified by silica gel column chromatography, and the title compound (0.98 mmol, 296 mg) was obtained in a 93% yield.

Workup

  1. additionwas poured into the reaction solution
  2. customto terminate
  3. customthe reaction
  4. extractionThe organic substances were extracted with ethyl acetate
  5. dry with materialthe obtained organic layer was dried over magnesium sulfate
  6. customthe solvents were evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6aa2c34e02934fac82b84827cda42325
Source dataset
uspto-grants-2012_07
Patent number
US08222429B2

Reaction notes

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