Pyridine → HCID 53628661, compound

HRID 2262616Notes

Reaction equation

HRID 2262616 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:13][N:12]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:11]2)=[N:8][CH:9]=1)([O-])=O.O.O.Cl[Sn]Cl.N1C=CC=CC=1.[CH:29]([C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1)([CH3:31])[CH3:30]>C(O)C.C(Cl)Cl>[CH:29]([C:32]1[CH:37]=[CH:36][C:35]([S:38]([NH:1][C:4]2[CH:9]=[N:8][C:7]([CH:10]3[CH2:13][N:12]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:11]3)=[CH:6][CH:5]=2)(=[O:40])=[O:39])=[CH:34][CH:33]=1)([CH3:31])[CH3:30]

Participants

7

Reactant 4

HCID 1049PyridineHCID 61436Stannous chloride dihydrateHCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 57470078HCID 57470078, compound

Product 1

HCID 53628661HCID 53628661, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-[3-(5-nitro-pyridin-2-yl)-azetidin-1-yl]-propan-1-one (340 mg, 1.44 mmol) was dissolved in ethanol (EtOH) (25 ml) and SnCl2.2H2O (1.63 g, 7.22 mmol) was added. The resulting mixture was refluxed for 8 h and the solvent next removed under vacuum. The raw material was dissolved in ethyl acetate and washed successively with 2N aqueous NaOH (×2) and water. The organic layer was dried (Na2SO4), filtered through a pad of celite and evaporated. Half of the crude material was then dissolved in CH2Cl2 (40 ml) and pyridine (115 μl, 1.41 mmol) followed by 4-isopropylbenzensulfonylchloride (190 μl, 1.05 mmol) were added dropwise. After stirring at room temperature overnight, the reaction mixture was diluted with CH2Cl2 and washed successively with 1N aqueous HCl, saturated aqueous NaHCO3 and water. The organic layer was dried (Na2SO4) and evaporated. The residue was chromatographied on silica gel (heptane:ethyl acetate, 1:3) to afford the title compound (150 mg, 54% for two steps) as a light yellow oil.

Workup

  1. temperatureThe resulting mixture was refluxed for 8 h
  2. customthe solvent next removed under vacuum
  3. dissolutionThe raw material was dissolved in ethyl acetate
  4. washwashed successively with 2N aqueous NaOH (×2) and water
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered through a pad of celite
  7. customevaporated
  8. dissolutionHalf of the crude material was then dissolved in CH2Cl2 (40 ml)
  9. additionwere added dropwise
  10. washwashed successively with 1N aqueous HCl, saturated aqueous NaHCO3 and water
  11. dry with materialThe organic layer was dried (Na2SO4)
  12. customevaporated

Sources & evidence

ORD record
ord-47a4ffc0ebf648718015956c6a62b78e
Source dataset
uspto-grants-2010_12
Patent number
US07851463B2

Reaction notes

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