Ethyl Acetate → 5-Nitro-7-azaindole

HRID 2261614Notes

Reaction equation

HRID 2261614 reaction equation
[CH3:1][C:2]1[C:3]([NH2:11])=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[C:12](OCC)(=O)C>>[N+:8]([C:6]1[CH:7]=[C:2]2[CH:1]=[CH:12][NH:11][C:3]2=[N:4][CH:5]=1)([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 27344462-Amino-3-methyl-5-nitropyridine

Product 1

HCID 115211405-Nitro-7-azaindole

Procedure

5-Nitro-1H-pyrrolo[2,3-b]pyridine 506 of is prepared by reacting 3-methyl-5-nitro-pyridin-2-ylamine 505 with t-butyloxycarbonyl anhydride in an appropriate solvent (e.g. ethyl acetate and hexanes). Concentration and extraction provides a Boc-protected intermediate that is then reacted with 2 equivalents of butyllithium in an appropriate polar solvent (e.g. tetrahydrofuran) with cooling (e.g. 0° C.), followed by the addition of dimethylformamide and stirring for 30 minutes to one hour, followed by addition of 5.5 M HCl. Isolation by conventional means (e.g. extraction and silica gel chromatography) provides 506. (Hands et. al., Synthesis 1996, 877-882.)

Workup

  1. concentrationConcentration and extraction

Sources & evidence

ORD record
ord-7476bb305116402b84f424f082c1355f
Source dataset
uspto-grants-2010_12
Patent number
US07846941B2

Reaction notes

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