2-(3,3-Difluoroazetidin-1-yl)-5-nitropyridine → HCID 52937165, compound

HRID 1019541Notes

Reaction equation

HRID 1019541 reaction equation
[F:1][C:2]1([F:15])[CH2:5][N:4]([C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][N:7]=2)[CH2:3]1.[H][H]>C(O)C.[Pd]>[NH2:12][C:9]1[CH:8]=[N:7][C:6]([N:4]2[CH2:5][C:2]([F:15])([F:1])[CH2:3]2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 529372622-(3,3-Difluoroazetidin-1-yl)-5-nitropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 52937165HCID 52937165, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 0.34 g (1.58 mmol) of 2-(3,3-difluoroazetidin-1-yl)-5-nitropyridine, prepared in the preceding stage, and 8 mg of Pd/C at 10% in 10 mL of ethanol is stirred vigorously at 20° C. under 5 atm of hydrogen for 4 hours. After this time, the mixture is filtered on a Celite pad, then concentrated at reduced pressure. The resultant product is purified by chromatography on a silica column, eluting with a mixture of dichloromethane and methanol. We thus obtain 0.188 g of the expected product in the form of a red powder, which is used as it is in the rest of the synthesis.

Workup

  1. filtrationAfter this time, the mixture is filtered on a Celite pad
  2. concentrationconcentrated at reduced pressure
  3. customThe resultant product is purified by chromatography on a silica column
  4. washeluting with a mixture of dichloromethane and methanol
  5. customis in the rest of the synthesis

Sources & evidence

ORD record
ord-e29d072b32eb4a999de1f73110091940
Source dataset
uspto-grants-2014_05
Patent number
US08716272B2

Reaction notes

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