Sodium hydride → 3-[(4-nitro-1H-indol-1-yl)methyl]-1H-pyrrolo[2,3-b]pyridine

HRID 240477Notes

Reaction equation

HRID 240477 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](=[CH:26][CH:27]=[CH:28][N:29]=2)[C:24]([CH2:31]Cl)=[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:24]1[C:25]2[C:30](=[N:29][CH:28]=[CH:27][CH:26]=2)[NH:22][CH:23]=1)([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1457664-Nitro-1H-indoleHCID 21463021tert-Butyl 3-(chloromethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 687480693-[(4-nitro-1H-indol-1-yl)methyl]-1H-pyrrolo[2,3-b]pyridineYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)-3-chloromethyl-7-azaindole (Int-14, 1.5 g, 5.5 mmol) was then added. Upon completion (by TLC), the reaction 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, and concentrated under reduced pressure to dryness. The residue was purified by flash column chromatography to provide 3-[(4-nitro-1H-indol-1-yl)methyl]-1H-pyrrolo[2,3-b]pyridine (547 mg, 34%).

Workup

  1. customUpon completion (by TLC), the reaction 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 to dryness
  8. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-a14fb79c515d46c9996406a4e19b82ca
Source dataset
uspto-grants-2014_02
Patent number
US08648086B2

Reaction notes

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