5-Bromoindole → 5-Bromoindoline

HRID 1504649Notes

Reaction equation

HRID 1504649 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[BH3-]C#N.[Na+]>C(O)(=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 249055-BromoindoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 34115665-BromoindolineYield 71%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To 5-Bromo-1H-indole (2.5 g, 12.82 mmol) in acetic acid (10.0 mL), NaCNBH3 (2.38 g, 38.46 mmol) was added portion wise at 10° C. over the period of 20 min. After that the reaction mixture was stirred at ambient temperature for 3 h. The reaction mixture was diluted with water and extracted with diethyl ether. The organic layer was washed with saturated NaHCO3, water and brine solution. The combined ether layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford title compound as a pale yellow semi-solid (1.8 g, 71%).

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with saturated NaHCO3, water and brine solution
  3. dry with materialThe combined ether layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c4cbc4eda9de4ad599c3af14d3ee8a85
Source dataset
uspto-grants-2015_12
Patent number
US09215870B2

Reaction notes

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