Benzyl Bromide → Benzyl 1H-indole-5-carboxylate

HRID 1406397Notes

Reaction equation

HRID 1406397 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(=O)(O)[O-].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH2:18]([O:11][C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2)=[O:12])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 742801H-Indole-5-Carboxylic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 10264164Benzyl 1H-indole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of indole-5-carboxylic acid (2.63 g, 16.34 mmol) in N,N-dimethylformamide (50 mL) was added sodium bicarbonate (8.24 g, 98.04 mmol) and benzyl bromide (11.66 mL, 98.04 mmol). The reaction was stirred for 48 hours at ambient temperature under nitrogen. The reaction was then partitioned between ethyl acetate and water. The organic layer was separated and the aqueous extracted with a further portion of ethyl acetate. The combined organic layers were dried (MgSO4) and evaporated in vacuo. The resultant crude product was purified by flash chromatography on SiO2, eluting with 20% ethyl acetate/hexane followed by 50% ethyl acetate/hexane to afford the title compound as an oil, 4.82 g, quantitative.

Workup

  1. customThe reaction was then partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. extractionthe aqueous extracted with a further portion of ethyl acetate
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. customevaporated in vacuo
  6. customThe resultant crude product was purified by flash chromatography on SiO2
  7. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-48cfa0265bff4482b06e0bfc1a576330
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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