Hydrochloric Acid → HCID 22143615, compound

HRID 985271Notes

Reaction equation

HRID 985271 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14](=[O:19])C(F)(F)F)=[C:4]1[CH3:20])[CH3:2].[OH-:21].[K+].Cl>C(O)C.O>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]([OH:19])=[O:21])=[C:4]1[CH3:20])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22143614HCID 22143614, compound

Product 1

HCID 22143615HCID 22143615, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(1-ethyl-6-methoxy-2-methyl-1H-indol-3-yl)-2,2,2-trifluoro-ethanone 71b (580 mg, 2.03 mmole) in 10 ml ethanol was added a solution of KOH (1.1 g, 20 mmole) in 10 ml water. The mixture was heated to reflux for 1 hour and cooled to room temperature. Concentrated HCl was added to adjust pH to 1. The mixture was extracted with EtOAc and the combined organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was further purified by column chromatography (eluting with 1-2% MeOH in CH2Cl2) to give 350 mg product as brown solid (74% yield). 1H NMR (400 MHz, CDCl3) δ8.07 (1H, d, J=8.7 Hz), 6.90 (1H, dd, J=2.2, 8.7 Hz), 6.80 (1H, d, J=2.2 Hz), 4.14 (2H, q, J=7.2 Hz), 3.88 (3H, s), 2.77 (3H, s), 1.37 (3H, t, J=7.2 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialthe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was further purified by column chromatography (eluting with 1-2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-c3989932534d43b6a9831d922fb123e7
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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