Water → 2-(3-Azabicyclo[3.1.0]hex-3-yl)-5-nitropyridine

HRID 506520Notes

Reaction equation

HRID 506520 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH:11]12[CH2:16][CH:15]1[CH2:14][NH:13][CH2:12]2.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:11]12[CH2:16][CH:15]1[CH2:14][N:13]([C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)[CH2:12]2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 131505233-Azabicyclo(3.1.0)hexane

Product 1

HCID 574315302-(3-Azabicyclo[3.1.0]hex-3-yl)-5-nitropyridineYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 0.2 g (1.26 mmol) of 2-chloro-5-nitropyridine, of 0.166 g (1.39 mmol) of 3-azabicyclo[3.1.0]hexane (Bioorg. &Med. Chem. Lett. 2005, 15(8) 2093) and of 0.52 g (3.78 mmol) of potassium carbonate in 5 ml of dimethylformamide is stirred at ambient temperature for 36 hours. The mixture is subsequently poured into 5 ml of water and then extracted 3 times with 20 ml of ethyl acetate. The organic phases are subsequently combined, dried over magnesium sulfate, and then concentrated under reduced pressure. 0.22 g of the expected product is thus obtained, which product is used as it is in the rest of the synthesis.

Workup

  1. extractionextracted 3 times with 20 ml of ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b68772a7870b44bd9bf480ec329360e9
Source dataset
uspto-grants-2010_08
Patent number
US07786104B2

Reaction notes

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