Sodium Hydroxide → HCID 57800167, compound

HRID 2101822Notes

Reaction equation

HRID 2101822 reaction equation
[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:18]([O:20]CC)=[O:19])[N:6]2[CH2:13][C:14]([F:17])([F:16])[F:15].[OH-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:18]([OH:20])=[O:19])[N:6]2[CH2:13][C:14]([F:17])([F:16])[F:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 24985292HCID 24985292, compound

Product 1

HCID 57800167HCID 57800167, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ethyl 4-chloro-5-cyano-1-(2,2,2-trifluoroethyl)-1H-indole-2-carboxylate (0.02 g, 0.06 mmol) in 1:1 THF/MeOH (4 mL) was added 1N NaOH (1 mL) and the mixture was heated at 70° C. for 1.25 h. Upon cooling, the mixture was partially concentrated under vacuo. The residue was partitioned between EtOAc and 0.2N HCl. The organic phase was washed with sat'd brine. The combined aqueous phases were reextracted twice with EtOAc. The organic phases were combined and washed with sat'd brine, dried (Na2SO4) and concentrated in vacuo to afford the title compound (0.017 g, 94% yield): MS (ES) m/z 301 (M−1).

Workup

  1. temperatureUpon cooling
  2. concentrationthe mixture was partially concentrated under vacuo
  3. customThe residue was partitioned between EtOAc and 0.2N HCl
  4. washThe organic phase was washed with sat'd brine
  5. washwashed with sat'd brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6753e17c5554f3e83b87fc70d29b631
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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