Toluene → HCID 57576766, compound

HRID 1777392Notes

Reaction equation

HRID 1777392 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[CH:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=2)[N:7]=1)=O)C.C1(C)C=CC=CC=1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1.[H-].C([Al+]CC(C)C)C(C)C>[F:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH:9]=[CH:10][C:6]([CH2:4][OH:3])=[N:7]2)=[N:12][CH:13]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 9855836Potassium sodium tartarateHCID 57576801HCID 57576801, compound

Product 1

HCID 57576766HCID 57576766, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21225700DiisobutylaluminumhydrideSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of ethyl-1-(5-fluoropyridin-2-yl)-1H-pyrazole-3-carboxylate obtained in Reference Example 27 (10.0 g, 42.5 mmol) in THF (50 mL), diisobutylaluminium hydride (a 1.01 mol/L toluene solution, 105.2 mL, 106.3 mmol) was added under cooling at −78° C., and after dropwise addition the resulting mixture was heated to 0° C. and stirred for 2 hours. An aqueous solution of potassium sodium tartrate (Rochelle salt) was added to the reaction mixture under ice-cooling, 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 to obtain the title compound (8.0 g) (colorless solid).

Workup

  1. additionwas added
  2. additionafter dropwise addition the resulting mixture
  3. temperaturewas heated to 0° C.
  4. temperaturecooling
  5. extractionfollowed by extraction with EtOAc
  6. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over MgSO4
  8. filtrationthe drying agent was filtered off
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b7d4ae777c4941b3a14700ff30d530f0
Source dataset
uspto-grants-2016_02
Patent number
US09266870B2

Reaction notes

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