Butyl bromide → HCID 21105401, compound

HRID 2426725Notes

Reaction equation

HRID 2426725 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, 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. additionwas added
  2. washwashed three times with water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (mobile phase ethyl acetate/heptane 1:6)
  6. dissolutionThe resulting ester was dissolved in methanol (10 ml)
  7. temperatureunder reflux with sodium hydroxide (0.6 g ) in water (10 ml) for 12 hours
  8. additionThe mixture was diluted with water
  9. extractionfollowed by extraction with ethyl acetate
  10. dry with materialThe organic phase was dried over magnesium sulfate
  11. concentrationconcentrated
  12. customThis resulted in the product with the molecular weight of 217.27 (C13H15NO2)

Sources & evidence

ORD record
ord-edef7e5504a947c089a802e1f3e6f118
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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