Sodium borohydride → HCID 59831715, compound

HRID 268751Notes

Reaction equation

HRID 268751 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:11][C:12]#[N:13])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[BH4-].[Na+]>CC(O)C>[NH:1]1[C:2]2[C:7](=[C:6]([CH:10]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:11][C:12]#[N:13])[CH:5]=[CH:4][CH:3]=2)[CH:8]=[CH:9]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride3×HCID 72573288HCID 72573288, compound

Product 1

HCID 59831715HCID 59831715, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent3×

Procedure

To a stirring suspension of 3-(1H-indol-5-yl)-3-phenyl-acrylonitrile VII (2.8 g, 11.5 mmol) in 2-propanol (60 ml) at room temperature, under N2 was added NaBH4 (2.8 g, 74 mmol) portionwise over 90 min period. The mixture was refluxed for 20 hours and additional 2-propanol (25 ml) was added to facilitate the stirring. After 40 hours at reflux, additional NaBH4 (0.5 g, 13.2 mmol) was added. After 60 hours at reflux, additional NaBH4 (1 g, 26.4 mmol) and 2-propanol (20 ml) were added. After 110 hours at reflux, the mixture was cooled to room temperature, concentrated and the residue was partitioned between H2O and Et2O. The organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated. The waxy dark yellow solid was re-subjected to the NaBH4 reduction conditions at reflux for 40 hours. The reaction was cooled to room temperature and worked up as above affording 3-(1H-indol-4-yl)-3-phenyl-propionitrile VIII as a yellow-brown solid which was used as crude mixture for the next reaction.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. temperatureAfter 40 hours at reflux
  3. temperatureAfter 60 hours at reflux
  4. temperatureAfter 110 hours at reflux
  5. concentrationconcentrated
  6. customthe residue was partitioned between H2O and Et2O
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. temperatureat reflux for 40 hours
  13. temperatureThe reaction was cooled to room temperature

Sources & evidence

ORD record
ord-da2881e2fdae4160826321cef20fa30d
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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