2-Chloro-3-nitropyridine → HCID 86604876, compound

HRID 1432010Notes

Reaction equation

HRID 1432010 reaction equation
[Cl-].[CH3:2][O:3][C:4](=[O:10])[C@H:5]([NH3+:9])[CH2:6][C:7]#[CH:8].Cl[C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=1>CS(C)=O>[N+:18]([C:17]1[C:12]([NH:9][C@H:5]([CH2:6][C:7]#[CH:8])[C:4]([O:3][CH3:2])=[O:10])=[N:13][CH:14]=[CH:15][CH:16]=1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 796132-Chloro-3-nitropyridine2×HCID 86760973HCID 86760973, compound

Product 1

HCID 86604876HCID 86604876, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(R)-1-methoxy-1-oxopent-4-yn-2-aminium chloride (6.16 g, 38 mmol) in DMSO (100 mL) added 2-chloro-3-nitropyridine (9.0 g, 56 mmol) and then 2-chloro-3-nitropyridine (9.0 g, 56 mmol). The reaction mixture was stirred for 5 d. EtOAC (500 mL) was added and the diluted reaction mixture was washed with 4×brine (200 mL), dried, evaporated to give 10 g of crude material which was purified by column chromatograph (silica gel, 20-100% hex/tolune, EtOAc) to give the title compound.

Workup

  1. additionEtOAC (500 mL) was added
  2. customthe diluted reaction mixture
  3. washwas washed with 4×brine (200 mL)
  4. customdried
  5. customevaporated
  6. customto give 10 g of crude material which
  7. customwas purified by column chromatograph (silica gel, 20-100% hex/tolune, EtOAc)

Sources & evidence

ORD record
ord-7f8ef7490e19439e84e2d0a12bd6806c
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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