Butyl bromide → HCID 21105401, compound

HRID 1354778Notes

Reaction equation

HRID 1354778 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14]C)=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.Br[CH2:17][CH2:18][CH2:19][CH3:20]>CN(C=O)C.C(OCC)(=O)C>[CH2:17]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1)[CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 21105401HCID 21105401, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (50% in oil, 1.4 g) was added to methyl 1H-indole-5-carboxylate (5.0 g) in DMF (100 ml) and, after gas evolution ceased, bromobutane (3.9 g) was added. After 12 hours, the reaction solution was diluted with ethyl acetate and washed three times with water. The organic phase was dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel (mobile phase ethyl acetate/heptane 1:6). The resulting ester was dissolved in methanol (10 ml) and boiled under reflux with sodium hydroxide (0.6 g ) in water (10 ml) for 12 hours. The mixture was diluted with water and acidified with hydrochloric acid, followed by extraction with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. This resulted in the product with the molecular weight of 217.27 (C13H15NO2); MS (ESI): 218 (M+H+).

Workup

  1. washwashed three times with water
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel (mobile phase ethyl acetate/heptane 1:6)
  5. dissolutionThe resulting ester was dissolved in methanol (10 ml)
  6. temperatureunder reflux with sodium hydroxide (0.6 g ) in water (10 ml) for 12 hours
  7. additionThe mixture was diluted with water
  8. extractionfollowed by extraction with ethyl acetate
  9. dry with materialThe organic phase was dried over magnesium sulfate
  10. concentrationconcentrated
  11. customThis resulted in the product with the molecular weight of 217.27 (C13H15NO2)

Sources & evidence

ORD record
ord-3c9f2671c2034ad591b8b51fb37e63d0
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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