Sodium borohydride → HCID 59831860, compound

HRID 268755Notes

Reaction equation

HRID 268755 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:11][C:12]#[N:13])[CH:8]=2)[CH:3]=[CH:2]1.[BH4-].[Na+]>CC(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][C:12]#[N:13])[CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 72573301HCID 72573301, compound

Product 1

HCID 59831860HCID 59831860, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

To a stirring suspension of 3-(1H-indol-6-yl)-3-phenyl-acrylonitrile XII (1.3 g, 5.3 mmol) in 2-propanol (30 ml), NaBH4 (1.3 g, 34 mmol) was added portionwise over 30 min. The mixture was heated at reflux for 110 hours while occasionally adding 2-propanol to maintain the original volume. The mixture was cooled to room temperature and concentrated. The residue was partitioned between Et2O and H2O. The organic layer was separated, washed with brine, dried over MgSO4, filtered and evaporated. The crude 3-(1H-indol-6-yl)-3-phenyl-propionitrile (1.2 g, 90% pure) was used without further purification for the next reaction.

Workup

  1. additionwas added portionwise over 30 min
  2. temperatureThe mixture was heated
  3. temperatureto maintain the original volume
  4. concentrationconcentrated
  5. customThe residue was partitioned between Et2O and H2O
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude 3-(1H-indol-6-yl)-3-phenyl-propionitrile (1.2 g, 90% pure) was used without further purification for the next reaction

Sources & evidence

ORD record
ord-78d6298329e448fab30b639aee5ad986
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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