5-Fluoroindole → 5-Fluoroindoline

HRID 1372427Notes

Reaction equation

HRID 1372427 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C([BH3-])#N.[Na+]>C(O)(=O)C.O.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2

Participants

6

Reactant 2

HCID 678615-FluoroindoleHCID 5003444Sodium cyanoborohydride

Product 1

HCID 27744635-Fluoroindoline

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

5-Fluoroindole (3 g, 22.2 mmol) in glacial acetic acid (35 mL) was treated with sodium cyanoborohydride (2.79 mg, 44.4 mmol) portionwise at room temperature with stirring. After one hour, the reaction was diluted with water and basified with 40% sodium hydroxide with cooling. The mixture was extracted 3 times with dichloromethane, dried and concentrated to give 5-fluoroindoline. It was used in the next step without further purification. 1H-NMR (300 MHz, dimethylsulfoxide-d6) δ 6.86 (m, 1H), 6.68 (dt, 1H), 6.42 (dd, 1H), 5.32 (br s, 1H, NH), 3.38 (m, 2H, CH2), 2.87 (t, 2H, CH2).

Workup

  1. temperaturewith cooling
  2. extractionThe mixture was extracted 3 times with dichloromethane
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bef285e33ef04233802d3b7e7e6da221
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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