Water → HCID 68777910, compound

HRID 2262965Notes

Reaction equation

HRID 2262965 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.N1C=CC=CC=1.Cl[C:18]([O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[O:19].O>O1CCCC1>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][C:18](=[O:19])[O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 788675-AminoindoleHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 68777910HCID 68777910, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-aminoindole (1.00 g, 7.57 mmol) and pyridine (0.720 ml, 9.08 mmol) in tetrahydrofuran (25 ml) was added, under ice-cooling, 2,2,2-trichloroethyl chloroformate (1.26 ml, 9.08 mmol), and the mixture was stirred at room temperature for 1 hour and half. Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by high performance liquid chromatography (YMC HPLC Column eluted with 10% to 100% Liquid A; Liquid A: a 0.1% solution of trifluoroacetic acid in acetonitrile; Liquid B: an aqueous 0.1% trifluoroacetic acid solution) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 334 mg (14.3%) of the desired product as a solid.

Workup

  1. temperaturecooling
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by high performance liquid chromatography (YMC HPLC Column
  7. washeluted with 10% to 100% Liquid A
  8. customLiquid B: an aqueous 0.1% trifluoroacetic acid solution) and recrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record
ord-a3e49bf7c6394e599c3d003963950bc6
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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