Sodium Bicarbonate → HCID 86686303, compound

HRID 406591Notes

Reaction equation

HRID 406591 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:11]1[C:12]([CH3:25])=[N:13][N:14]([CH3:24])[C:15]=1[C:16]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=1[F:23])O.COCCN(S(F)(F)[F:36])CCOC.C(=O)(O)[O-].[Na+]>ClCCl>[F:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([F:22])[C:16]=1[C:15]1[N:14]([CH3:24])[N:13]=[C:12]([CH3:25])[C:11]=1[CH:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])[F:36]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 66613811HCID 66613811, compound

Product 1

HCID 86686303HCID 86686303, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of α-(2,4-difluorophenyl)-5-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole-4-methanol (i.e. the product of Example 4) (70 mg, 0.20 mmol) in dichloromethane (2 mL) at −78° C. was added bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor®) (40 μL, 0.24 mmol). The reaction mixture was stirred overnight at room temperature, and then cooled to −78° C. and saturated aqueous sodium bicarbonate solution (3 mL) was added dropwise. The resulting mixture was extracted with dichloromethane (3×) and the combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting material was purified by MPLC (50% ethyl acetate in hexanes as eluant) to provide the title compound, a compound of the present invention, as a solid (30 mg)

Workup

  1. temperaturecooled to −78° C.
  2. extractionThe resulting mixture was extracted with dichloromethane (3×)
  3. dry with materialthe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting material was purified by MPLC (50% ethyl acetate in hexanes as eluant)

Sources & evidence

ORD record
ord-75a28a72a73b4fc4838f754f8649731e
Source dataset
uspto-grants-2014_06
Patent number
US08754115B2

Reaction notes

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