Sodium borohydride → HCID 86686304, compound

HRID 406593Notes

Reaction equation

HRID 406593 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[C:12]([CH3:25])=[N:13][N:14]([CH3:24])[C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[F:23])=[O:10].[BH4-].[Na+]>C(O)C>[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[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=1[F:23])[OH:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66613393HCID 66613393, compound

Product 1

HCID 86686304HCID 86686304, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of (2,4-difluorophenyl)-[5-(2,4-difluorophenyl)-1,3-dimethyl-1H-pyrazol-4-yl]methanone (i.e. the product of Example 7) (80 mg, 0.23 mmol) in ethanol (3 mL) at about 0° C. was added sodium borohydride (38 mg, 0.92 mmol). The reaction mixture was stirred at room temperature for 2 h, and then diluted with ice/hydrochloric acid (about 1 mL). The resulting mixture was poured onto a solid phase extraction tube (Varian Chem Elute®, prepacked with diatomaceous earth) eluting with ethyl acetate (75 mL). The ethyl acetate eluant was concentrated under reduced pressure and the resulting material was purified by MPLC (20 to 70% gradient of ethyl acetate in hexanes as eluant) to provide the title compound, a compound of the present invention, as a solid (63 mg).

Workup

  1. additionThe resulting mixture was poured onto a solid phase extraction tube (Varian Chem Elute®, prepacked with diatomaceous earth)
  2. washeluting with ethyl acetate (75 mL)
  3. concentrationThe ethyl acetate eluant was concentrated under reduced pressure
  4. customthe resulting material was purified by MPLC (20 to 70% gradient of ethyl acetate in hexanes as eluant)

Sources & evidence

ORD record
ord-d933960d14f04ba68ea0c35f58c5a611
Source dataset
uspto-grants-2014_06
Patent number
US08754115B2

Reaction notes

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