Sodium borohydride → HCID 86680236, compound

HRID 1428807Notes

Reaction equation

HRID 1428807 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:31])[C:10]([NH:12][CH2:13][C:14]2[C:15]([C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=2)=[O:11])=[CH:5][C:4]=1[CH3:32])#[N:2].[BH4-].[Na+]>C(O)C>[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:31])[C:10]([NH:12][CH2:13][C:14]2[C:15]([C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)=[N:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=2)=[O:11])=[CH:5][C:4]=1[CH3:32]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86680235HCID 86680235, compound

Product 1

HCID 86680236HCID 86680236, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2-(4-cyano-3-methylphenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (147 mg, 0.34 mmol) in ethanol was cooled to 0° C. and added NiCl2.6H2O (80 mg, 0.34 mmol) and stirred more than 15 mins. Sodium borohydride (81 mg, 2.35 mmol) was then added in small portions. The reaction was exothermic and effervescent. The resulting reaction mixture was allowed to warm to room temperature and left to stir for 2 h. The mixture was filtered using celite pad. The filtrate was concentrated was evaporated. The residue was dissolved in ethylacetate and washed with water and brine, but when it does not separate easily, small amount of 1N HCl and saturated NaHCO3 was used. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(4-(Aminomethyl)-3-methylphenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (83 mg) was obtained as 56% yield.

Workup

  1. customThe resulting reaction mixture
  2. waitleft
  3. stirringto stir for 2 h
  4. filtrationThe mixture was filtered
  5. concentrationThe filtrate was concentrated
  6. customwas evaporated
  7. dissolutionThe residue was dissolved in ethylacetate
  8. washwashed with water and brine, but when it
  9. customdoes not separate easily
  10. dry with materialThe organic layer was dried over magnesium sulfate
  11. filtrationfiltered
  12. customThe filtrate removed in vacuo
  13. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-3d9ec69e839940fababd37e467fc42da
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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