2-Chloro-3-nitropyridine → HCID 68901106, compound

HRID 735355Notes

Reaction equation

HRID 735355 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18]([O-:20])=[O:19])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1.[Na+].Cl[C:23]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=1>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([S:18]([C:23]2[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=2)(=[O:20])=[O:19])[CH:12]=[CH:11]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 796132-Chloro-3-nitropyridineHCID 68900681Sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate

Product 1

HCID 68901106HCID 68901106, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate (154 mg, 0.50 mmol), 2-chloro-3-nitropyridine (79 mg, 0.50 mmol) and DMSO (2.5 mL) were combined and the resulting solution stirred at ambient temperature for 19 hours. The solution was partitioned between EtOAc (25 mL) and water (25 mL) and the organic layer was subsequently washed with brine (15 mL), dried (MgSO4), filtered and concentrated in vacuo to afford semi-pure 2-{[6-(4-fluorophenyl)naphthalen-2-yl]sulfonyl}-3-nitropyridine as a yellow solid (189 mg) which was used directly in the following step. 1H NMR (500 MHz, d6-DMSO): δ 8.85 (1H, dd, J=1.3, 4.6 Hz), 8.75-8.73 (1H, m), 8.63 (1H, dd, J=1.3, 8.1 Hz), 8.38 (2H, t, J=7.7 Hz), 8.25 (1H, d, J=8.8 Hz), 8.06 (1H, dd, J=1.7, 8.6 Hz), 7.98-7.92 (4H, m), 7.39 (2H, t, J=8.8 Hz).

Workup

  1. customThe solution was partitioned between EtOAc (25 mL) and water (25 mL)
  2. washthe organic layer was subsequently washed with brine (15 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d922f30e85f4ac6825e6d58c1608ecd
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

Loading…