Sodium borohydride → HCID 118432152, compound

HRID 2207986Notes

Reaction equation

HRID 2207986 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]3[N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:27])[N:19]=[C:18]([C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[F:30])[CH2:17]3)[CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N:20]1[CH:16]([C:12]2[CH:11]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([CH:1]([OH:3])[CH3:2])=[CH:5][CH:6]=3)[CH:15]=[CH:14][CH:13]=2)[CH2:17][C:18]([C:28]([F:34])([F:33])[C:29]([F:30])([F:31])[F:32])=[N:19]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118431627HCID 118431627, compound

Product 1

HCID 118432152HCID 118432152, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4′-Acetyl-biphenyl-3-yl)-1-(2-chloro-phenyl)-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole (18.0 mg, 0.04 mmol) prepared in Example 107 and sodium borohydride (2.0 mg, 0.06 mmol) were added at 0° C. to methanol (2.0 mL). The reaction mixture was stirred at room temperature for 3 hours, quenched with distilled water, 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 17.0 mg of the titled compound as a yellow liquid.

Workup

  1. customquenched with distilled water
  2. extractionextracted with ethyl acetate three times
  3. extractionThe combined extract
  4. washwas washed with brine
  5. dry with materialdried on anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c37e63e0c9854eabadb75c5caf0f3736
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

Loading…