Water → HCID 59673820, compound

HRID 1391427Notes

Reaction equation

HRID 1391427 reaction equation
B(O)O.[F:4][C:5]([F:14])([F:13])[C:6]1[C:7](Cl)=[N:8][CH:9]=[CH:10][CH:11]=1.O.[C:16]([O-:19])([O-])=[O:17].[K+].[K+].[C:22](#N)[CH3:23]>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.[Pd]>[F:4][C:5]1[CH:6]=[C:11]([CH:10]=[CH:22][C:23]=1[C:7]1[C:6]([C:5]([F:14])([F:13])[F:4])=[CH:11][CH:10]=[CH:9][N:8]=1)[C:16]([OH:19])=[O:17]

Participants

7

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 61668Boronic AcidHCID 5898332-Chloro-3-(trifluoromethyl)pyridine

Product 1

HCID 59673820HCID 59673820, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 178527696HCID 178527696, compoundCatalyst

Procedure

The boronic acid (2.45 mmol) was dissolved in acetonitrile (2.4 ml) and 3-(trifluoromethyl)-2-chloropyridine was added. After mixing, tetrakis palladium was added (25 mg; 0.01 mol %), follwed by 0.8 ml of water and K2CO3 (912 mg; 3.0 mmol). The reaction mixture was heated at 160° C. in a Personal Chemistry Emrys Microwave for 300s. After reaction completion, the solvents were evaporated and the residue was dissolved in EtOAc and washed with water and brine. The organic layer was dried over MgSO4, filtered and evaporated. The residue was then dissolved in a 1:1 mixture of THF/2NKOH and heated until saponification was complete. The basic layer was then extracted with EtOAc and acidified with conc.HCl. The aqueos layer was then extracted three times with EtOAc. The combined organic layers were dried over MgSO4, filtered and evaporated to give the desired material as a white solid (530 mg; 76%).

Workup

  1. additionAfter mixing
  2. customAfter reaction completion
  3. customthe solvents were evaporated
  4. dissolutionthe residue was dissolved in EtOAc
  5. washwashed with water and brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. dissolutionThe residue was then dissolved in a 1:1 mixture of THF/2NKOH
  10. temperatureheated until saponification
  11. extractionThe basic layer was then extracted with EtOAc
  12. extractionThe aqueos layer was then extracted three times with EtOAc
  13. dry with materialThe combined organic layers were dried over MgSO4
  14. filtrationfiltered
  15. customevaporated

Sources & evidence

ORD record
ord-fa5673563c0c4903b54920fa7699bf37
Source dataset
uspto-grants-2008_03
Patent number
US07338950B2

Reaction notes

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