Azetidine → HCID 68682086, compound

HRID 1952218Notes

Reaction equation

HRID 1952218 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:17]1[CH2:20][CH2:19][CH2:18]1>C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[N:17]1([C:2]2[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=2)[CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 3

HCID 10422AzetidineHCID 10796Cesium carbonateHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 68682086HCID 68682086, compoundYield 62.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

1 g of 5-bromo-2-nitropyridine, 3.5 g of cesium carbonate, 825 mg of bis(diphenylphosphino)ferrocene, 110 mg of palladium acetate and 15 ml of toluene are charged to a microwave tube and then 424 mg of azetidine are added. The tube is stirred and heated in a bath at 105° C., and then left at ambient temperature for 16 h. The reaction mixture is filtered and the solid is rinsed with dichloromethane. The combined filtrates are concentrated to dryness under reduced pressure and the residue is chromatographed on a silica cartridge, elution being carried out with dichloromethane. The fractions comprising the expected product are combined and concentrated to dryness under reduced pressure to give 550 mg of 5-(azetidin-1-yl)-2-nitropyridine in the form of a yellow solid.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe solid is rinsed with dichloromethane
  3. concentrationThe combined filtrates are concentrated to dryness under reduced pressure
  4. customthe residue is chromatographed on a silica cartridge, elution
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-0ac82b7cae884cc684dcfc8247a8ee11
Source dataset
uspto-grants-2013_03
Patent number
US08404848B2

Reaction notes

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