Water → HCID 67508709, compound

HRID 623487Notes

Reaction equation

HRID 623487 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].Cl[C:6]1[N:19]=[C:18]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])[CH:17]=[CH:16][C:7]=1[C:8]([O:10][CH2:11][C:12](F)(F)F)=[O:9].O>O1CCCC1>[CH2:2]([O:1][C:6]1[N:19]=[C:18]([O:20][CH2:21][C:22]([F:25])([F:23])[F:24])[CH:17]=[CH:16][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 87426801HCID 87426801, compound

Product 1

HCID 67508709HCID 67508709, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium ethoxide (1.4 mL, 3.55 mmol, 20% in ethanol) is added to a solution of 2,2,2-trifluoroethyl 2-chloro-6-(2,2,2-trifluoroethoxy)nicotinate (400 mg, 1.19 mmol, Step-1 of Amine-37) in tetrahydrofuran (15 mL) and stirred at room temperature for 1 hour. The reaction mixture is poured into water and extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-Hexane/ethyl acetate (7:1) to give 305 mg (88% yield) of title compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by column chromatography on silica gel eluting with n-Hexane/ethyl acetate (7:1)

Sources & evidence

ORD record
ord-b15c6333fd074e20b562afa91ad427f7
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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