Water → HCID 19609782, compound

HRID 1602051Notes

Reaction equation

HRID 1602051 reaction equation
C[O-].[K+].[F:4][C:5]1[C:6]([O:34][C:35]2[N:39]([CH3:40])[N:38]=[C:37]([C:41]([F:44])([F:43])[F:42])[CH:36]=2)=[N:7][C:8]([O:23][C:24]2[N:28]([CH3:29])[N:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)=[C:9]([F:22])[C:10]=1[O:11][C:12]1N(C)N=C(C(F)(F)F)C=1.O>CO>[CH3:40][N:39]1[C:35]([O:34][C:6]2[C:5]([F:4])=[C:10]([O:11][CH3:12])[C:9]([F:22])=[C:8]([O:23][C:24]3[N:28]([CH3:29])[N:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[CH:25]=3)[N:7]=2)=[CH:36][C:37]([C:41]([F:44])([F:42])[F:43])=[N:38]1

Participants

5

Reactant 3

HCID 962WaterHCID 15869764HCID 15869764, compoundHCID 23664618Potassium methoxide

Product 1

HCID 19609782HCID 19609782, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 25% solution of potassium methylate in dry methanol (4.4 ml, 15 mmol) is added to a solution of 3,5-difluoro-2,4,6-tris (1-methyl-3-trifluoromethylpyrazol-5-yloxy)pyridine (9.1 g, 15 mmol; see (a) above) in dry methanol (50 ml). After 30 min at ambient temperature the reaction is stopped by adding 2 ml of water. The solvent is removed under reduced pressure and pentane/ethyl acetate (1/1 by volume) is added to the residue. After filtration through a bed of silica gel the filtrate is washed with a 2 N sodium hydroxide solution. After drying and filtration of the organic layer, the solvents are removed and the residue is washed with diisopropyl ether. One obtains colorless crystals (5.3 g 75% yield), m.p. 83° C.

Workup

  1. customThe solvent is removed under reduced pressure and pentane/ethyl acetate (1/1 by volume)
  2. additionis added to the residue
  3. filtrationAfter filtration through a bed of silica gel the filtrate
  4. washis washed with a 2 N sodium hydroxide solution
  5. customAfter drying
  6. filtrationfiltration of the organic layer
  7. customthe solvents are removed
  8. washthe residue is washed with diisopropyl ether
  9. customOne obtains colorless crystals (5.3 g 75% yield), m.p. 83° C.

Sources & evidence

ORD record
ord-48d0734e8b1f4fd097bd02b9f6ef8fdb
Source dataset
uspto-grants-1999_11
Patent number
US05981437

Reaction notes

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