Sodium borohydride → HCID 118431962, compound

HRID 2207975Notes

Reaction equation

HRID 2207975 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:21]=[C:22]([CH:28]=[O:29])[C:23]([O:26][CH3:27])=[N:24][CH:25]=3)[CH:15]=2)[CH2:12][C:11]([C:30]([F:36])([F:35])[C:31]([F:34])([F:33])[F:32])=[N:10]1.[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:25]=[N:24][C:23]([O:26][CH3:27])=[C:22]([CH2:28][OH:29])[CH:21]=3)[CH:15]=2)[CH2:12][C:11]([C:30]([F:36])([F:35])[C:31]([F:34])([F:32])[F:33])=[N:10]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118432063HCID 118432063, compound

Product 1

HCID 118431962HCID 118431962, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(2,4-difluoro-phenyl)-5-(3-(3-formyl-2-methoxy-pyridin-5-yl)-phenyl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole (20 mg, 0.04 mmol) prepared in Example 73 in ethanol (1 mL), was slowly added sodium borohydride (6.0 mg, 0.16 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 hour, quenched with a 1N hydrochloric acid solution, and then extracted with ethyl acetate three times. The combined extract was washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a residue as a pale yellow liquid. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/1) to give 3.0 mg of the titled compound as a white solid.

Workup

  1. customat 0° C
  2. customquenched with a 1N hydrochloric acid solution
  3. extractionextracted with ethyl acetate three times
  4. extractionThe combined extract
  5. washwas washed with brine
  6. dry with materialdried on anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b0533fb45d62429b9b97ae2197bb3c69
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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