Methyl iodide → 1-Methyl-4-nitro-1H-pyrrolo[2,3-b]pyridine

HRID 2240233Notes

Reaction equation

HRID 2240233 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[NH:12][CH:13]=[CH:14][C:7]=12)([O-:5])=[O:4].[CH3:15]I>CC(N(C)C)=O>[CH3:15][N:12]1[C:8]2=[N:9][CH:10]=[CH:11][C:6]([N+:3]([O-:5])=[O:4])=[C:7]2[CH:14]=[CH:13]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 6392484-Nitro-7-azaindole

Product 1

HCID 593050251-Methyl-4-nitro-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

170 mg (4.29 mmol) of sodium hydride are added to a solution of 500 mg (3.06 mmol) of 4-nitro-1H-pyrrolo[2,3-b]pyridine (Antonini, Ippolito; Claudi, Francesco; Cristalli, Gloria; Franchetti, Palmarisa; Grifantini, Mario; Martelli, Sante; J. Med. Chem. 1982, 25, 1258-1261.) in 10 ml of absolute DMA, and the suspension is stirred for 30 min. A solution of 230 μl (3.68 mmol) of methyl iodide in 2 ml of absolute DMA is then slowly added dropwise, and the mixture is again stirred for 60 min. After concentration under reduced pressure, the residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1).

Workup

  1. stirringthe mixture is again stirred for 60 min
  2. concentrationAfter concentration under reduced pressure
  3. customthe residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-98480131891e46e5906bc224961c01e5
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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