Sodium hydride → 1-(2,6-difluoro-4-nitrophenyl)-3-iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine

HRID 2206234Notes

Reaction equation

HRID 2206234 reaction equation
[I:1][C:2]1[C:6]2[C:7]([O:11][CH3:12])=[N:8][CH:9]=[CH:10][C:5]=2[NH:4][CH:3]=1.C1OCCOCCOCCOCCOC1.[H-].[Na+].[F:30][C:31]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[C:33]([F:40])[C:32]=1F>CN(C=O)C>[F:30][C:31]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[C:33]([F:40])[C:32]=1[N:4]1[C:5]2[CH:10]=[CH:9][N:8]=[C:7]([O:11][CH3:12])[C:6]=2[C:2]([I:1])=[CH:3]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 27827931,2,3-Trifluoro-5-nitrobenzeneHCID 247294143-Iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 1179883961-(2,6-difluoro-4-nitrophenyl)-3-iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine (200 mg) in DMF (6 ml) were added 15-crown-5 (0.159 ml) and sodium hydride (60% dispersion in mineral oil, 32.1 mg), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added 1,2,3-trifluoro-5-nitrobenzene (0.101 ml), and the mixture was stirred overnight at room temperature under nitrogen atmosphere. The reaction mixture was extracted with water and ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (258 mg).

Workup

  1. stirringthe mixture was stirred overnight at room temperature under nitrogen atmosphere
  2. extractionThe reaction mixture was extracted with water and ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-119291fef59c4f8ebb663a72f7e40544
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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