Hydrochloric Acid → 5-Bromo-4-methoxy-1H-pyrrolo[2,3-b]pyridine

HRID 2088975Notes

Reaction equation

HRID 2088975 reaction equation
[CH3:1][O-:2].[K+].C[O-].[Li+].[Br:7][C:8]1[C:9](Cl)=[C:10]2[CH:16]=[CH:15][NH:14][C:11]2=[N:12][CH:13]=1.Cl>C1(C)C(C)=CC=CC=1.C(O)(C)(C)C>[Br:7][C:8]1[C:9]([O:2][CH3:1])=[C:10]2[CH:16]=[CH:15][NH:14][C:11]2=[N:12][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4177230Lithium methanolateHCID 23664618Potassium methoxideHCID 457897885-Bromo-4-chloro-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 575374785-Bromo-4-methoxy-1H-pyrrolo[2,3-b]pyridineYield 25.2%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
117 °C

Procedure

Potassium methoxide (103 mg), lithium methoxide (27 mg) and tert-butanol (40 μl) were added to a solution of 5-bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (81 mg) in xylene (3.5 ml), and the mixture was heated under reflux at 117° C. for 16 hours. The reaction solution was brought to pH 4 by adding concentrated hydrochloric acid in small portions and separated by adding ethyl acetate and distilled water. The resulting aqueous layer was brought to pH 8 by adding a 5 N aqueous sodium hydroxide solution and separated by adding ethyl acetate. All the resulting organic layers were combined, washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by thin-layer chromatography (developed with ethyl acetate-hexane) to give the title compound (20 mg).

Workup

  1. temperaturethe mixture was heated
  2. customseparated
  3. additionby adding ethyl acetate
  4. distillationdistilled water
  5. additionby adding a 5 N aqueous sodium hydroxide solution
  6. customseparated
  7. additionby adding ethyl acetate
  8. washwashed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customThe resulting residue was purified by thin-layer chromatography (developed with ethyl acetate-hexane)

Sources & evidence

ORD record
ord-ca02cc1b28c24d32be702b1c9f079438
Source dataset
uspto-grants-2013_05
Patent number
US08436012B2

Reaction notes

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