Potassium Carbonate → HCID 54736358, compound

HRID 2195624Notes

Reaction equation

HRID 2195624 reaction equation
C([O-])([O-])=O.[K+].[K+].[OH:7][C:8]1[C:9]([C:14]([O:16]C2C(F)=C(F)C(F)=C(F)C=2F)=O)=[N:10][CH:11]=[CH:12][CH:13]=1.[F:28][C:29]([F:42])([F:41])[O:30][C:31]1[CH:32]=[C:33]([CH2:37][C:38](Cl)=[O:39])[CH:34]=[CH:35][CH:36]=1>C(#N)C.O>[OH:16][C:14]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[O:7][C:38](=[O:39])[C:37]=1[C:33]1[CH:34]=[CH:35][CH:36]=[C:31]([O:30][C:29]([F:28])([F:41])[F:42])[CH:32]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 86102346HCID 86102346, compoundHCID 86656541HCID 86656541, compound

Product 1

HCID 54736358HCID 54736358, compoundYield 44.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
22.5 °C

Procedure

3.5 g of K2CO3 were added to a solution of 0.64 g of pentafluorophenyl 3-hydroxy-pyridine-2-carboxylate (from step 1) and 0.5 g of (3-trifluoromethoxyphenyl)acetyl chloride in 150 ml of acetonitrile, and the mixture was stirred at 20-25° C. under an atmosphere of nitrogen for about 12 hours. After filtration, the solvent was removed from the filtrate and the residue obtained was taken up in water and, after acidification to pH<4, extracted with CH2Cl2. The organic phase was dried, then freed from the solvent. The residue gave, after preparative HPLC [column: Luna (2), from Phenomenex, 300*50 mm 10 μm; mobile phase: water (+0.0375% trifluoroacetic acid) and acetonitrile in mixing ratios of 80:20 and 50:50; flow rate 80 ml/min; detection at 220 and 254 nm), 20-25° C.], 300 mg of the title compound.

Workup

  1. filtrationAfter filtration
  2. customthe solvent was removed from the filtrate
  3. customthe residue obtained
  4. extractionafter acidification to pH<4, extracted with CH2Cl2
  5. customThe organic phase was dried
  6. customThe residue gave
  7. custom20-25° C.

Sources & evidence

ORD record
ord-c16b11456c0142cfbf1793373d5a44a4
Source dataset
uspto-grants-2012_12
Patent number
US08338337B2

Reaction notes

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