Sodium borohydride → HCID 57762786, compound

HRID 230634Notes

Reaction equation

HRID 230634 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[C:13]([C:20]([F:23])([F:22])[F:21])=[N:12]2)=[CH:6][CH:5]=1)([O-])=O.[BH4-].[Na+]>CO.[Pd].O>[F:23][C:20]([F:21])([F:22])[C:13]1[C:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=2[N:11]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)[N:12]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 57762790HCID 57762790, compound

Product 1

HCID 57762786HCID 57762786, compoundYield 44.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-[(4-nitrophenyl)methyl]-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (410 mg, 1.26 mmol) in methanol (3 ml) was added dropwise to a stirred suspension of 10% palladium on charcoal in water (1.3 ml) containing sodium borohydride (95 mg, 2.50 mmol), under argon with cooling. The resulting mix was stirred at room temperature for 1 hour. The reaction mix was filtered and then acidified using 2M HCl to destroy any excess sodium borohydride, and then basified again using 2M aqueous sodium hydroxide. The mix was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulphate and the solvent removed under reduced pressure to give a yellow oil, which was chromatographed on a 5 g pre-packed silica column eluting from 0-20% ethyl acetate in petroleum ether to give the title compound as a yellow oil (166 mg, 43%).

Workup

  1. temperatureunder argon with cooling
  2. additionThe resulting mix
  3. additionThe reaction mix
  4. filtrationwas filtered
  5. customto destroy any excess sodium borohydride
  6. customThe mix was partitioned between ethyl acetate and water
  7. dry with materialThe organic layer was dried over sodium sulphate
  8. customthe solvent removed under reduced pressure
  9. customto give a yellow oil, which
  10. customwas chromatographed on a 5 g pre-packed silica column
  11. washeluting from 0-20% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-01217fc79ed4453cbea3d61b93000d3f
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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