5-Fluoroindole → 5-Fluoroindoline

HRID 1276528Notes

Reaction equation

HRID 1276528 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 separated, 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 separated
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-b712509d9ac64bd5a964a0e69ed7d6c3
Source dataset
uspto-grants-2000_12
Patent number
US06166064

Reaction notes

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