Pyridine → 4-Ethyl-7,8-difluoro-5-[(4-methoxy-3-methylphenyl)sulfonyl]-4,5-dihydropyrrolo[1,2-a]quinoxaline

HRID 229373Notes

Reaction equation

HRID 229373 reaction equation
[CH2:1]([CH:3]1[NH:12][C:11]2[C:6](=[CH:7][C:8]([F:14])=[C:9]([F:13])[CH:10]=2)[N:5]2[CH:15]=[CH:16][CH:17]=[C:4]12)[CH3:2].N1C=CC=CC=1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][C:27]=1[CH3:36]>C(Cl)Cl>[CH2:1]([CH:3]1[N:12]([S:32]([C:29]2[CH:30]=[CH:31][C:26]([O:25][CH3:24])=[C:27]([CH3:36])[CH:28]=2)(=[O:34])=[O:33])[C:11]2[C:6](=[CH:7][C:8]([F:14])=[C:9]([F:13])[CH:10]=2)[N:5]2[CH:15]=[CH:16][CH:17]=[C:4]12)[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 159153174-Methoxy-3-methylbenzene-1-sulfonyl chlorideHCID 690616264-Ethyl-7,8-difluoro-4,5-dihydropyrrolo[1,2-a]quinoxaline

Product 1

HCID 690662264-Ethyl-7,8-difluoro-5-[(4-methoxy-3-methylphenyl)sulfonyl]-4,5-dihydropyrrolo[1,2-a]quinoxalineYield 72.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.35 g (5.0 mmol) of the product from Example 3 was dissolved in 40 ml of methylene chloride and 1 ml of pyridine added. To this solution was added 1.20 g (5.4 mmol) of 4-methoxy-3-methyl benzenesulfonyl chloride. The solution was stirred at room temperature for 6 hours, after which it was concentrated, then diluted with 5 ml of 2N HCl. The residue was extracted 2 times with ethyl acetate, dried (MgSO4) and concentrated. The crude solid so obtained was chromatographed on silica gel, eluting with 20% ethyl acetate:hexane to afford a light yellow solid, which can be recrystallized from ethyl acetate:hexane to yield 1.52 g (72%) of product.

Workup

  1. concentrationafter which it was concentrated
  2. additiondiluted with 5 ml of 2N HCl
  3. extractionThe residue was extracted 2 times with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude solid so obtained
  7. customwas chromatographed on silica gel
  8. washeluting with 20% ethyl acetate
  9. customhexane to afford a light yellow solid, which
  10. customcan be recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3adbaaa62d81467f849bc7be3fe41a5e
Source dataset
uspto-grants-2009_07
Patent number
US07563793B2

Reaction notes

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