Methanol → HCID 58100944, compound

HRID 1948789Notes

Reaction equation

HRID 1948789 reaction equation
[OH-].[K+].[CH3:3][Si:4]([CH3:28])([CH3:27])[C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[N:12]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=1)[C:11]([C:22]([O:24]CC)=[O:23])=[CH:10]2.CO.O>O1CCOCC1>[CH3:3][Si:4]([CH3:28])([CH3:27])[C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[N:12]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=1)[C:11]([C:22]([OH:24])=[O:23])=[CH:10]2

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14797Potassium HydroxideHCID 66850507HCID 66850507, compound

Product 1

HCID 58100944HCID 58100944, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.23 g (4.06 mmol) of potassium hydroxide is added to a solution of 0.5 g (1.35 mmol) of ethyl 7-trimethylsilyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxylate, obtained according to the protocol described in stage 5.2, in 30 ml of a mixture (v/v/v) of methanol, water and dioxane. After stirring at reflux for three hours, the reaction mixture is one-third concentrated under reduced pressure and then taken up in 10 ml of water. The medium is acidified at pH 1 by successive additions of 1N hydrochloric acid. The precipitate is recovered by filtration, washed with water and then dried under reduced pressure. 0.37 g of the expected product is thus isolated, which product is used as it is in the subsequent stage.

Workup

  1. customobtained
  2. temperatureat reflux for three hours
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe precipitate is recovered by filtration
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-c838337d24d349a79e9dc2b4c19173c0
Source dataset
uspto-grants-2013_03
Patent number
US08399491B2

Reaction notes

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