Sodium cyanoborohydride → HCID 57800413, compound

HRID 2101919Notes

Reaction equation

HRID 2101919 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[C:11]([C:12]#[N:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[CH2:14][C:15]1[N:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[O:17][N:16]=1.[BH3-]C#N.[Na+]>C(O)(C(F)(F)F)=O>[F:31][C:2]([F:1])([F:30])[C:3]1[C:11]([C:12]#[N:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][N:7]2[CH2:14][C:15]1[N:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:28])([F:29])[F:27])[CH:21]=2)[O:17][N:16]=1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 24983832HCID 24983832, compound

Product 1

HCID 57800413HCID 57800413, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To an ice-cold solution of 4-(trifluoromethyl)-1-({5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-1H-indole-5-carbonitrile (Example 60D) (0.025 g, 0.057 mmol) in TFA (1 mL) was added NaCNBH3 (0.050 g, 0.79 mmol) in portions. After addition, the mixture was stirred at rt for 3 h and then concentrated in vacuo. The residue was partitioned between CH2Cl2 and 0.2N NaOH. The organic phase was washed with water and sat'd brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (0-30% EtOAc-hexanes gradient) and the product was crystallized from CH2Cl2-hexanes to give the title compound as a white solid (0.013 g, 52% yield): MS (ES) m/z 439 (M+1).

Workup

  1. additionAfter addition
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between CH2Cl2 and 0.2N NaOH
  4. washThe organic phase was washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (0-30% EtOAc-hexanes gradient)
  8. customthe product was crystallized from CH2Cl2-hexanes

Sources & evidence

ORD record
ord-ec02bcf55ebf4a4b976a9fe2df109c6b
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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