Benzyl Bromide → HCID 751130, compound

HRID 1069568Notes

Reaction equation

HRID 1069568 reaction equation
CCCCCC.[CH3:7][C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([N+:17]([O-:19])=[O:18])=[CH:12][CH:11]=2.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[CH3:7][C:8]1[N:9]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([N+:17]([O-:19])=[O:18])=[CH:12][CH:11]=2

Participants

5

Reactant 3

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

Product 1

HCID 751130HCID 751130, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 mol) 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. washto wash 80 mg 2.0 mmol) of 60% NaH/mineral oil and 6 mL of DMF
  2. additionwas added
  3. extractionThe mixture was extracted with EtOAc
  4. washthe EtOAc washed with a saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. concentrationon concentrating at reduced pressure, crystals
  7. customformed
  8. washThese were washed with MeOH

Sources & evidence

ORD record
ord-73dd2ff83c37430880b7e67881051aeb
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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