Benzyl Bromide → 1-Benzyl-1H-indole-4-carbonitrile

HRID 1777723Notes

Reaction equation

HRID 1777723 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]#[N:11])[C:4]=2[CH:3]=[CH:2]1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+]>CN(C=O)C>[CH2:12]([N:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]#[N:11])[C:4]=2[CH:3]=[CH:2]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 38176024-Cyanoindole

Product 1

HCID 290120411-Benzyl-1H-indole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of indole-4-carbonitrile (2.0 g, 14.1 mmol, 1 eq) and benzyl bromide (2.17 mL, 18.3 mmol, 1.3 eq) in dry DMF (20 mL) was added, at rt, NaH (733 mg, 18.3 mmol, 1.3 eq) portionwise under Ar(g). The resulting reaction mixture was stirred at rt overnight, and was subsequently partitioned with H2O (30 mL), and then extracted with EtOAc (3×20 mL) and CH2Cl2 (20 mL). The combined organic extracts were dried over MgSO4 and the solvent was removed in vacuo. The residue was further purified by silica gel column chromatography with hexane/EtOAc (9:1-1:3) to furnish the product, 2, as a white solid (3.30 g, 99%).

Workup

  1. customThe resulting reaction mixture
  2. customwas subsequently partitioned with H2O (30 mL)
  3. extractionextracted with EtOAc (3×20 mL) and CH2Cl2 (20 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customThe residue was further purified by silica gel column chromatography with hexane/EtOAc (9:1-1:3)
  7. customto furnish the product, 2

Sources & evidence

ORD record
ord-424348a1a8794a57adcde51b968d75db
Source dataset
uspto-grants-2016_02
Patent number
US09266879B2

Reaction notes

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