Sodium borohydride → HCID 86686304, compound

HRID 2276023Notes

Reaction equation

HRID 2276023 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-fd74c54c7b344b398605464be29f17bd
Source dataset
uspto-grants-2015_09
Patent number
US09131693B2

Reaction notes

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