5-Bromoindole → 5-Bromoindoline

HRID 1992337Notes

Reaction equation

HRID 1992337 reaction equation
[BH3-]C#N.[Na+].[Br:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2>C(O)(=O)C>[Br:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 249055-BromoindoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 34115665-Bromoindoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

NaBH3CN (19.3 g, 0.3061 mol) was added in 3 portions to a cooled (15° C.) solution of 5-bromoindole (20 g, 0.10 mol) in glacial acetic acid (500 mL) and stirred for 2 h at this same temperature. The reaction mixture was quenched with water, cooled and basified with a sodium hydroxide pellet. It was then extracted with diethyl ether. The organic layer was washed with water and brine, dried over sodium sulfate, concentrated and purified by column chromatography over silica gel to give the sub-title compound as a pale yellow solid. Yield: 20 g.

Workup

  1. customThe reaction mixture was quenched with water
  2. temperaturecooled
  3. extractionIt was then extracted with diethyl ether
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by column chromatography over silica gel

Sources & evidence

ORD record
ord-15ed5aa6e9724c6ebe7e3e4c39d1e8a5
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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