Ethyl Acetate → HCID 178428363, compound

HRID 384092Notes

Reaction equation

HRID 384092 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([C:5]1[C:6](F)=[N:7][CH:8]=[CH:9][C:10]=1I)=O.O.[NH2:16][NH2:17].[CH3:18]COC(C)=O.C([O-])(O)=O.[Na+].[Cl-].[Na+].O>O1CCOCC1>[CH3:18][C:10]1[CH:9]=[CH:8][N:7]=[C:6]2[NH:16][N:17]=[C:3]([C:2]([F:14])([F:13])[F:1])[C:5]=12

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 579695632,2,2-Trifluoro-1-(2-fluoro-4-iodopyridin-3-yl)ethanoneHCID 129703874Sodium hydrogencarbonate brine

Product 1

HCID 178428363HCID 178428363, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

2,2,2-trifluoro-1-(2-fluoro-4-iodo-3-pyridyl)ethanone (40 g, 125.4 mmol) was dissolved in 1,4-dioxane (300 mL). Hydrazine monohydrate (18.83 g, 18.30 mL, 376.2 mmol) was added dropwise and the mixture heated to 90° C. for 90 minutes. The mixture was cooled and poured into EtOAc (800 ml) and 3:1 sat NaHCO3/brine (500 ml). The organic layer was separated and the aqueous extracted with EtOAc (3×50 ml). The combined organics were washed with brine (100 ml), dried (MgSO4), filtered and concentrated. The residue was slurried in DCM (50 ml) and the resultant white solid was isolated by filtration, washed with DCM and dried (28.7 g, 73% Yield).

Workup

  1. temperatureThe mixture was cooled
  2. customThe organic layer was separated
  3. extractionthe aqueous extracted with EtOAc (3×50 ml)
  4. washThe combined organics were washed with brine (100 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe resultant white solid was isolated by filtration
  9. washwashed with DCM
  10. customdried (28.7 g, 73% Yield)

Sources & evidence

ORD record
ord-4901dfd1a75b45fcb8ecd6b25d0228f7
Source dataset
uspto-grants-2013_02
Patent number
US08367697B2

Reaction notes

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