Sodium hydride → HCID 68749054, compound

HRID 240473Notes

Reaction equation

HRID 240473 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2)([O-:5])=[O:4].C(OC([N:22]1[C:30]2[C:25](=[C:26]([CH2:31]Cl)[CH:27]=[CH:28][N:29]=2)[CH:24]=[CH:23]1)=O)(C)(C)C>C1COCC1>[N+:3]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][N:10]2[CH2:31][C:26]1[CH:27]=[CH:28][N:29]=[C:30]2[NH:22][CH:23]=[CH:24][C:25]=12)([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1457664-Nitro-1H-indoleHCID 67041431HCID 67041431, compound

Product 1

HCID 68749054HCID 68749054, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was also prepared according to the following method. Specifically, sodium hydride (144 mg, 6 mmol) was added to a solution of 4-nitroindole (973 mg, 6 mmol) in THF and the resulting mixture was stirred for 4 h. 1-(t-butyloxycarbonyl)-4-chloromethyl-7-azaindole (Int-11, 1.5 g, 5.5 mmol) was then added. After the reaction was complete (by TLC), the mixture was quenched with saturated aqueous ammonium chloride. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by flash column chromatography to provide 4-[(4-nitro-1H-indol-1-yl)methyl]-1H-pyrrolo[2,3-b]pyridine (254 mg, 16%).

Workup

  1. customthe mixture was quenched with saturated aqueous ammonium chloride
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-879beefdebae4d33a279950311c57c7a
Source dataset
uspto-grants-2014_02
Patent number
US08648086B2

Reaction notes

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