Benzyl Bromide → Ethyl 1-benzyl-5-bromo-1H-indole-2-carboxylate

HRID 1724026Notes

Reaction equation

HRID 1724026 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Br:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2].[H-].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[NH4+].[Cl-]>CN(C=O)C.CCOCC>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Br:15])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 259091Ethyl 5-Bromoindole-2-carboxylate

Product 1

HCID 21964289Ethyl 1-benzyl-5-bromo-1H-indole-2-carboxylateYield 98.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5 g (19 mmol) of 5-bromoindol-2-carboxylic acid ethyl ester in 20 mL of anhydrous DMF was added portionwise 1.06 g (24 mmol) of NaH (55% in oil). The mixture was stirred at RT for 45 minutes, treated dropwise with 2.9 mL (24 mmol) of benzyl bromide and stirred for three hours. After addition of a saturated aqueous solution of NH4Cl and Et2O, the phases were separated and the aqueous one was extracted with Et2O. The combined organic phases were dried over Na2SO4 and evaporated to yield 6.7 g (98%) of crude 5-bromo-1-benzylindole-2-carboxylic acid ethyl ester, orange oil, MS: 358 (MH+).

Workup

  1. stirringstirred for three hours
  2. customthe phases were separated
  3. extractionthe aqueous one was extracted with Et2O
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-812bf6aa613041aea4411a5ab7c9bd5a
Source dataset
uspto-grants-2009_02
Patent number
US07485652B2

Reaction notes

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