Hydrochloric Acid → Ethyl 1H-pyrrolo(2,3-b)pyridine-2-carboxylate

HRID 857454Notes

Reaction equation

HRID 857454 reaction equation
O[C:2]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]1C(OC(C)(C)C)=O.Cl>C(O)C>[NH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][N:5]=2)[CH:10]=[C:2]1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 218687431-(tert-Butyl) 2-ethyl 2-hydroxy-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1,2-dicarboxylate

Product 1

HCID 21868741Ethyl 1H-pyrrolo(2,3-b)pyridine-2-carboxylateYield 71.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of (RS) ethyl (2-hydroxy-1-tert-butoxycarbonyl-7-azaindoline-2-carboxylate) (0.6 g, 1.9 mmol) in ethanol (20 mL) was added dropwise concentrated hydrochloric acid (0.6 mL). The mixture was heated under reflux for 2 h, cooled to room temperature and partitioned between ether (30 mL) and aqueous sodium hydrogen carbonate solution (30 mL). The organic layer was washed (water, brine), dried (sodium sulfate) and concentrated in vacuo to give ethyl 7-azaindole-2-carboxylate as a white solid (0.26 g, 70%). mp 153–6° C. Found: C, 62.84; H, 5.34; N, 14.50%. C10H10N2O2 requires: C, 63.15; H, 5.30; N, 14.72%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. custompartitioned between ether (30 mL) and aqueous sodium hydrogen carbonate solution (30 mL)
  4. washThe organic layer was washed (water, brine)
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76314ba6d49c4f4c81d01864dcc99933
Source dataset
uspto-grants-2006_12
Patent number
US07145009B2

Reaction notes

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