Potassium Carbonate → 1-(6-Nitro-pyridin-3-yl)-azetidin-3-ol

HRID 2359602Notes

Reaction equation

HRID 2359602 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.Cl.[NH:12]1[CH2:15][CH:14]([OH:16])[CH2:13]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O>[N+:8]([C:5]1[N:6]=[CH:7][C:2]([N:12]2[CH2:15][CH:14]([OH:16])[CH2:13]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 8176205-Bromo-2-nitropyridineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 86584982Sodium bicarbonate ethyl acetate

Product 1

HCID 592909581-(6-Nitro-pyridin-3-yl)-azetidin-3-olYield 29.5%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-2-nitropyridine (0.54 g, 2.66 mmol), azetidin-3-ol hydrochloride (0.46 g, 4.17 mmol) and tetrabutylammonium iodide (0.103 g, 0.278 mmol) in 6 mL of DMSO is added potassium carbonate (1.06 g, 7.68 mmol). The resulting mixture is heated to 80° C. for 3 h. Poured into ethyl acetate/NaHCO3 solution. Extracted with ethyl acetate (2×250 mL). The organic layer is ished with brine and dried over Na2SO4. Concentrated to give 1-(6-nitro-pyridin-3-yl)-azetidin-3-ol (153 mg, 29%). MS (ESI) m/z 240.1 (M+H)+

Workup

  1. extractionExtracted with ethyl acetate (2×250 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationConcentrated

Sources & evidence

ORD record
ord-12c8cf47dafc4803b14839066f279bf7
Source dataset
uspto-grants-2014_04
Patent number
US08685980B2

Reaction notes

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