Hydrochloric Acid → HCID 57930899, compound

HRID 1096972Notes

Reaction equation

HRID 1096972 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH:16]1([N:19]2[C:27]3[C:22](=[C:23](O)[CH:24]=[C:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:26]=3)[CH:21]=[CH:20]2)[CH2:18][CH2:17]1.N1C=CC=CC=1.Cl>C(Cl)(Cl)Cl>[CH:16]1([N:19]2[C:27]3[C:22](=[C:23]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:24]=[C:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:26]=3)[CH:21]=[CH:20]2)[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 57930939ethyl 1-cyclopropyl-4-hydroxy-1H-indole-6-carboxylate

Product 1

HCID 57930899HCID 57930899, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In a 500-mL egg plant-type flask, a chloroform (50 mL) solution of trifluoromethanesulfonic acid anhydride (6.30 mL, 37.5 mmol) was dropwise added to a chloroform (100 mL) solution of ethyl 1-cyclopropyl-4-hydroxy-1H-indole-6-carboxylate (6.12 g, 25 mmol) and pyridine (6.06 mL, 75 mmol) with cooling with ice, and stirred at that temperature for 30 minutes, then poured into aqueous hydrochloric acid solution, extracted with chloroform, washed with aqueous saturated sodium hydrogencarbonate solution, and dried with sodium sulfate. The reaction solution was filtered, concentrated, and purified through silica gel column chromatography (Biotage [SiO2, 40+M]) with a hexane/ethyl acetate developer system to obtain the title compound as a colorless oil.

Workup

  1. temperaturewith cooling with ice
  2. extractionextracted with chloroform
  3. washwashed with aqueous saturated sodium hydrogencarbonate solution
  4. dry with materialdried with sodium sulfate
  5. filtrationThe reaction solution was filtered
  6. concentrationconcentrated
  7. custompurified through silica gel column chromatography (Biotage [SiO2, 40+M]) with a hexane/ethyl acetate developer system

Sources & evidence

ORD record
ord-dced52c8d6914ed7837b41d107416894
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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