Sodium hydride → HCID 59304979, compound

HRID 2240217Notes

Reaction equation

HRID 2240217 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:12]([O:14][CH2:15]C)=[O:13].[H-].[Na+].[Cl:19][C:20]1[N:25]=[C:24]2[N:26]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH:27]=[CH:28][C:23]2=[C:22]([N+]([O-])=O)[CH:21]=1>CN(C=O)C>[Cl:19][C:20]1[N:25]=[C:24]2[N:26]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH:27]=[CH:28][C:23]2=[C:22]([CH:11]([C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[F:1])[C:12]([O:14][CH3:15])=[O:13])[CH:21]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 469416086-Chloro-4-nitro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridineHCID 56776686Ethyl (2-fluoro-4-nitrophenyl)acetate

Product 1

HCID 59304979HCID 59304979, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

908 mg (4.26 mmol) of ethyl (2-fluoro-4-nitrophenyl)acetate are dissolved in 10 ml of DMF, and 170 mg (4.26 mmol) of sodium hydride (60% in mineral oil) are added. The mixture is stirred at RT for 30 min, and 698 mg (2.13 mmol) of 6-chloro-4-nitro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine are then added. The mixture is heated at 70° C. for 2 hours and then stirred into ice-water and extracted with ethyl acetate. The organic phase is washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The product is purified by chromatography on silica gel (mobile phase: dichloromethane/pentane 2:1).

Workup

  1. temperatureThe mixture is heated at 70° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe product is purified by chromatography on silica gel (mobile phase: dichloromethane/pentane 2:1)

Sources & evidence

ORD record
ord-d733d2109d7d4021b5c71a5315044115
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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