Water → HCID 67991756, compound

HRID 1777382Notes

Reaction equation

HRID 1777382 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[N:11][N:12](C(OC(C)(C)C)=O)[CH:13]=2)O1.Br[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]=1.C([O-])([O-])=O.[Na+].[Na+].O>O1CCOCC1.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>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:9]2[CH:13]=[N:12][NH:11][CH:10]=2)=[N:24][CH:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27831712-Bromo-5-fluoropyridineHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate

Product 1

HCID 67991756HCID 67991756, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (15.4 g, 52.5 mmol) and 2-bromo-5-fluoropyridine (8.4 g, 47.7 mmol) in 1,4-dioxane (100 mL), Pd(PPh3)4 (5.5 g, 4.77 mmol) and a 2M aqueous solution of Na2CO3 (71.6 mL, 0.14 mol) were added, then the resulting mixture was stirred at 100° C. for 3 hours and then at room temperature for 72 hours. Water was added to the reaction mixture, followed by extraction with EtOAc. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over MgSO4, then the drying agent was filtered off, and then the solvent was distilled off under reduced pressure. A small amount of EtOAc was added to the obtained residue and the resulting mixture was filtered out and dried to obtain the title compound (4.9 g) (colorless solid).

Workup

  1. waitat room temperature for 72 hours
  2. extractionfollowed by extraction with EtOAc
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over MgSO4
  5. filtrationthe drying agent was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionA small amount of EtOAc was added to the obtained residue
  8. filtrationthe resulting mixture was filtered out
  9. customdried

Sources & evidence

ORD record
ord-c7b5921ded8f4efa98c2386484f967d8
Source dataset
uspto-grants-2016_02
Patent number
US09266870B2

Reaction notes

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