Benzyl Alcohol → benzyl-6-bromo-1H-indole-3-carbonitrile

HRID 871093Notes

Reaction equation

HRID 871093 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]#[N:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C(P(CCCC)(CCCC)=CC#N)CCC.[CH2:29](O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1(C)C=CC=CC=1>[CH2:29]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:10]=2)[C:6]([C:11]#[N:12])=[CH:7]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 4622928CyanomethylenetributylphosphoraneHCID 114700676-Bromo-1H-indole-3-carbonitrile

Product 1

HCID 90409858benzyl-6-bromo-1H-indole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 6-bromo-1H-indole-3-carbonitrile (400 mg, 1.81 mmol), 2-(tributylphosphoranylidene)acetonitrile (655 mg, 2.71 mmol) and benzyl alcohol (282 μL, 2.71 mmol) in toluene (5 mL) was heated at 75° C. overnight and concentrated. The residue was purified by flash chromatography on silica (IntelliFlash Varian 971-FP), eluting with 30% heptanes in ethyl acetate to provide the title compound. LCMS: 312.4 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography on silica (IntelliFlash Varian 971-FP)
  3. washeluting with 30% heptanes in ethyl acetate

Sources & evidence

ORD record
ord-d542bc628572477b804f6df8f0b43531
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

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