Water → HCID 67235649, compound

HRID 1505389Notes

Reaction equation

HRID 1505389 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=2[C:19]([F:22])([F:21])[F:20])=[N:8][CH:9]=1)([O-])=O.O.[NH4+].[Cl-]>C1COCC1.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=2[C:19]([F:22])([F:20])[F:21])=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 67236621HCID 67236621, compound2×

Product 1

HCID 67235649HCID 67235649, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[(5-nitro-2-pyridinyl)oxy]-3-(trifluoromethyl)benzonitrile (Intermediate 120, 83 mg) in THF (3 mL)/water (1.5 mL) was added at room temperature, iron (75 mg, 1.34 mmol) and NH4Cl (72 mg, 1.34 mmol) and the resulting reaction mixture was stirred overnight. The mixture was filtered through a small pad of celite washing with EtOAc and water. To the filtered mixture was added an aqueous NaHCO3 saturated solution and the two phases were separated. The aqueous phase was extracted with EtOAc and the combined organic phases were dried and evaporated to dryness. The crude was purified by flash chromatography (companion system, 2×12 g Si cartridge, from 100:0 to 70:30 Cyclohexane/EtOAc) to afford the title compound (72 mg).

Workup

  1. filtrationThe mixture was filtered through a small pad of celite
  2. washwashing with EtOAc and water
  3. additionTo the filtered mixture was added an aqueous NaHCO3 saturated solution
  4. customthe two phases were separated
  5. extractionThe aqueous phase was extracted with EtOAc
  6. customthe combined organic phases were dried
  7. customevaporated to dryness
  8. customThe crude was purified by flash chromatography (companion system, 2×12 g Si cartridge, from 100:0 to 70:30 Cyclohexane/EtOAc)

Sources & evidence

ORD record
ord-4eba1f24c8294ebdbb057a4df6aa47eb
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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