5-Fluoroindole → 5-Fluoroindoline

HRID 2303581Notes

Reaction equation

HRID 2303581 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>CCOCC.[BH4-].[Zn+2].[BH4-]>[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

4

Reactant 1

HCID 678615-Fluoroindole

Product 1

HCID 27744635-FluoroindolineYield 102.1%

Reagents, catalysts & solvents 2

HCID 12838295ZINC;boranuideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 6.8 grams (0.05 moles) of 5-fluoro-1H-indole in 50 ml of ether was cooled to 0° C. under nitrogen. 507 ml of a 0.15M solution of zinc borohydride in ether was added dropwise. The reaction was allowed to stir for 48 hours. The reaction was quenched with dilute hydrochloric acid. The pH was adjusted to 8.0 with dilute sodium hydroxide. The ether layer was seperated, dried and evaporated to give 7 grams of the titled compound.

Workup

  1. customThe reaction was quenched with dilute hydrochloric acid
  2. customThe ether layer was seperated
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-c13c4fd079e74505897f41b276172e3b
Source dataset
uspto-grants-2002_08
Patent number
US06433009B1

Reaction notes

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