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

HRID 2088963Notes

Reaction equation

HRID 2088963 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.[Br:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25]([C:30]([OH:32])=[O:31])=[CH:24]2>C(#N)C>[Br:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25]([C:30]([O:32][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:31])=[CH:24]2

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2521375-Bromo-1H-indole-2-carboxylic acid

Product 1

HCID 67077949benzyl 5-bromo-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl bromide (160 μl) and 1,8-diazabicyclo[5.4.0]undec-7-ene (201 μl) were added to a solution of 5-bromo-1H-indole-2-carboxylic acid (161 mg) in acetonitrile (3.5 ml) at room temperature, followed by stirring for 22.5 hours. The reaction solution was concentrated and separated by adding ethyl acetate and distilled water. The resulting organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was solidified from dichloromethane-hexane, collected by filtration and washed with hexane. This was dried under reduced pressure to give the title compound (189 mg).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customseparated
  3. additionby adding ethyl acetate
  4. distillationdistilled water
  5. washThe resulting organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. filtrationcollected by filtration
  9. washwashed with hexane
  10. customThis was dried under reduced pressure

Sources & evidence

ORD record
ord-0e7bbabd566a4ba9ab915e6e3be2b56a
Source dataset
uspto-grants-2013_05
Patent number
US08436012B2

Reaction notes

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