Benzyl Bromide → HCID 751130, compound

HRID 2292765Notes

Reaction equation

HRID 2292765 reaction equation
CCCCCC.[H-].[Na+].[CH3:9][C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([N+:19]([O-:21])=[O:20])=[CH:14][CH:13]=2.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O.CN(C=O)C>[CH3:9][C:10]1[N:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([N+:19]([O-:21])=[O:20])=[CH:14][CH:13]=2

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8058HexaneHCID 24758Sodium hydrideHCID 2803132-Methyl-5-nitro-1H-indole

Product 1

HCID 751130HCID 751130, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Hexane was used to wash 80 mg (2.0 mmol) of 60% NaH/mineral oil and 6 mL of DMF was added followed by 352 mg (2.0 mmol) of 2-methyl-5-nitro-1H-indole. After 0.33 hours, 0.24 mL (2.0 mmol) of benzyl bromide was added, stirred 0.5 hours and diluted with water. The mixture was extracted with EtOAc, the EtOAc washed with a saturated NaCl solution, dried MgSO4) and on concentrating at reduced pressure, crystals formed. These were washed with MeOH to give 400 mg (75% yield) of 2-methyl-5-nitro-1-(phenylmethyl)-1H-indole, mp, 150°-152° C.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with EtOAc
  3. washthe EtOAc washed with a saturated NaCl solution, dried MgSO4) and
  4. concentrationon concentrating at reduced pressure, crystals
  5. customformed
  6. washThese were washed with MeOH

Sources & evidence

ORD record
ord-6c5331b8c41244ee919f1157702086db
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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