Pyrrole → 3-Methoxy-6-(pyrrole-1-sulfonyl)-pyridazine

HRID 2101463Notes

Reaction equation

HRID 2101463 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.F[S:9]([C:12]1[N:13]=[N:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)(=[O:11])=[O:10]>CN(C=O)C>[CH3:19][O:18][C:15]1[N:14]=[N:13][C:12]([S:9]([N:3]2[CH:7]=[CH:6][CH:5]=[CH:4]2)(=[O:11])=[O:10])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8027PyrroleHCID 24758Sodium hydrideHCID 110306363-Fluorosulfonyl-6-methoxypyridazine

Product 1

HCID 120717773-Methoxy-6-(pyrrole-1-sulfonyl)-pyridazineYield 30.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To an ice-cold suspension of sodium hydride (1.86 mmol, 74 mg) in DMF (1 mL) was added a solution of pyrrole (1.86 mmol, 125 mg) in DMF (2 mL). To this was added 3-fluorosulfonyl-6-methoxypyridazine (1.55 mmol, 298 mg) and the reaction mixture was stirred overnight at room temperature. The reaction mixture was quenched with H2O (20 mL) and EtOAc (20 mL) and the EtOAc layer was collected, dried, filtered and evaporated to a residue. The residue was purified by silica gel chromatography (eluent: hexanes:EtOAc::9:1) to obtain 3-methoxy-6-(pyrrole-1-sulfonyl)-pyridazine (30%, 112 mg).

Workup

  1. customThe reaction mixture was quenched with H2O (20 mL) and EtOAc (20 mL)
  2. customthe EtOAc layer was collected
  3. customdried
  4. filtrationfiltered
  5. customevaporated to a residue
  6. customThe residue was purified by silica gel chromatography (eluent: hexanes:EtOAc::9:1)

Sources & evidence

ORD record
ord-32253191bc5b4d539446e2df9dcd1d68
Source dataset
uspto-grants-2009_08
Patent number
US07572910B2

Reaction notes

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