Benzyl Bromide → HCID 53765180, compound

HRID 653142Notes

Reaction equation

HRID 653142 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([C:16]=1[O:17][CH3:18])=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH3:4].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10]2[C:15]([C:16]=1[O:17][CH3:18])=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 12490854HCID 12490854, compound

Product 1

HCID 53765180HCID 53765180, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A mixture of 4.6 g (0.096 mole) of 50% sodium hydride/mineral oil in 100 ml of N,N-dimethylformamide under a nitrogen atmosphere was cooled in an ice bath. To the stirred mixture was added over 45 minutes, a solution of 19.5 g (0.089 mole) of 3-methoxy-1H-indole-2-carboxylic acid ethyl ester [A. Galun, A. Markus, and A. Kampf, J. Heterocyclic Chem., 16, 221 (1979)] in 50 ml of N,N-dimethylformamide. The mixture was stirred for an additional 30 minutes, and a solution of 11.6 ml (16.7 g; 0.098 mole) of benzyl bromide in 10 ml of N,N-dimethylformamide was added over 15 minutes. The ice bath was removed, the mixture was stirred for an additional 16 hours, and then added to 800 g of ice water. The crude ester intermediate was removed by extracting with dichloromethane (4×250 ml). The combined organic layers were back-washed with brine (3×500 ml), dried (anhydrous sodium sulfate), and evaporated to yield a crude residue of 3-methoxy-1(phenylmethyl)-1H-indole-2-carboxylic acid ethyl ester, plus a small amount of N,N-dimethylformamide.

Workup

  1. temperaturewas cooled in an ice bath
  2. additionTo the stirred mixture was added over 45 minutes
  3. customThe ice bath was removed
  4. stirringthe mixture was stirred for an additional 16 hours
  5. additionadded to 800 g of ice water
  6. customThe crude ester intermediate was removed
  7. extractionby extracting with dichloromethane (4×250 ml)
  8. washThe combined organic layers were back-washed with brine (3×500 ml)
  9. dry with materialdried (anhydrous sodium sulfate)
  10. customevaporated

Sources & evidence

ORD record
ord-94a3cea464ee4832a894cb1328021cd7
Source dataset
uspto-grants-1987_06
Patent number
US04675332

Reaction notes

Loading…