3-Nitropyridine → 6-Azaindole

HRID 731600Notes

Reaction equation

HRID 731600 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.[CH:10]([Mg]Br)=[CH2:11]>C1COCC1>[NH:1]1[C:4]2[C:9](=[CH:8][CH:7]=[N:6][CH:5]=2)[CH:11]=[CH:10]1

Participants

4

Reactant 2

HCID 1376303-NitropyridineHCID 178418507HCID 178418507, compound

Product 1

HCID 92196-Azaindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 3-nitropyridine in THF at −78° C. is treated with vinyl magnesium bromide (3 eq), stirred at −20° C. for 8 h and quenched with 20% ammonium chloride. The phases are separated and the aqueous phase is extracted with EtOAc. The organic phase and the combined extracts are mixed together, dried over MgSO4 and concentrated in vacuo. The resultant residue is chromatographed over silica gel to afford the title 6-azaindole.

Workup

  1. customquenched with 20% ammonium chloride
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with EtOAc
  4. additionThe organic phase and the combined extracts are mixed together
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-bb8cadeaf8024cf5b1bfb40dd98c6bc1
Source dataset
uspto-grants-2009_09
Patent number
US07585876B2

Reaction notes

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