Boron tribromide → 1-cyclopropyl-6-hydroxy-1H-indole-3-carbonitrile

HRID 1009662Notes

Reaction equation

HRID 1009662 reaction equation
[CH:1]1([N:4]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([O:13]C)[CH:11]=3)[C:6]([C:15]#[N:16])=[CH:5]2)[CH2:3][CH2:2]1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:1]1([N:4]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=3)[C:6]([C:15]#[N:16])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 594252703-Cyano-1-cyclopropyl-6-methoxyindole

Product 1

HCID 594306891-cyclopropyl-6-hydroxy-1H-indole-3-carbonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-cyclopropyl-6-methoxy-1H-indole-3-carbonitrile (3.60 g, 17.0 mmol) in CH2Cl2 (50.0 mL) was cooled to −78° C. and treated with BBr3 (21.27 g, 8.03 mL, 84.9 mmol), stirred for 10 min and then brought to room temperature and stirred for additional 30 minutes. The reaction mixture was poured into ice-water (150 mL), neutralized with NaHCO3 and the precipitate was collected by filtration, washed with water and purified on silica gel (CH2Cl2/EtOAc, 9:1) to provide 1-cyclopropyl-6-hydroxy-1H-indole-3-carbonitrile as a solid (3.02 g, 90%).

Workup

  1. custombrought to room temperature
  2. stirringstirred for additional 30 minutes
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with water
  5. custompurified on silica gel (CH2Cl2/EtOAc, 9:1)

Sources & evidence

ORD record
ord-bdca32b83ace439fae758a2c0d921d23
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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