Sodium Hydroxide → HCID 57800167, compound

HRID 1188315Notes

Reaction equation

HRID 1188315 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-0e9f1376d9124b1dbb8bd7f4b2662058
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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