Sodium borohydride → 2-(4-(aminomethyl)-3-fluorophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

HRID 1428783Notes

Reaction equation

HRID 1428783 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[F:32])#[N:2].[BH4-].[Na+]>C(O)C.[NiH6-5]Cl>[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[F:32]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 866802252-(4-cyano-3-fluorophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

Product 1

HCID 866802262-(4-(aminomethyl)-3-fluorophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

Reagents, catalysts & solvents 2

HCID 178479586HCID 178479586, compoundCatalystHCID 702EthanolSolvent

Procedure

Nickel(II) chloride hexahydride (1 equiv.) and 2-(4-cyano-3-fluorophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide are stirred in anhydrous ethanol during 15 minute for activation. Sodium borohydrid (7 equiv.) is added on it and mixture stirred for 2 h. Adding celite to the reaction and filter it using celite packed filter, washing with ethanol. The reaction mixture is purified after concentration to obtain 2-(4-(aminomethyl)-3-fluorophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide.

Workup

  1. additionAdding celite
  2. customto the reaction
  3. filtrationfilter it
  4. filtrationusing celite packed filter
  5. washwashing with ethanol
  6. customThe reaction mixture is purified
  7. concentrationafter concentration

Sources & evidence

ORD record
ord-0ed009c570f74694a781f48e9162d621
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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