Water → HCID 68969887, compound

HRID 492209Notes

Reaction equation

HRID 492209 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[Cl:11][C:12]([Cl:17])([Cl:16])[C:13](Cl)=[O:14].N1C=CC=CC=1.O>O1CCOCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:13](=[O:14])[C:12]([Cl:17])([Cl:16])[Cl:11])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6420Trichloroacetyl chlorideHCID 3512786-Fluoroindole

Product 1

HCID 68969887HCID 68969887, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

4.37 g (32.32 mmol) of 6-fluoroindole are added at a temperature in the region of 20° C. under an argon atmosphere to a solution of 4 cm3 (35.55 mmol) of trichloroacetyl chloride in 44.5 cm3 of 1,4-dioxane and 2.9 cm3 (35.55 mmol) of pyridine. After stirring at a temperature in the region of 20° C. for 20 hours, the reaction mixture is poured into 125 cm3 of demineralised water. The precipitate which appears is isolated by filtration, washed with 3 times 20 cm3 of water and then dried at 40° C. under reduced pressure to provide 5 g of 6-fluoro-3-trichloroacetyl-1H-indole in the form of a purple powder melting at 244° C.

Workup

  1. customThe precipitate which appears is isolated by filtration
  2. washwashed with 3 times 20 cm3 of water
  3. customdried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-4b98e18a2de840ab904e472901af825b
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

Loading…