ethyl 1H-pyrrolo[2,3-c]pyridine-2-carboxylate → HCID 20158234, compound

HRID 2080540Notes

Reaction equation

HRID 2080540 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]>C(O)(=O)C.[Rh]>[NH:1]1[C:5]2[CH2:6][NH:7][CH2:8][CH2:9][C:4]=2[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 1

HCID 21819001ethyl 1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Product 1

HCID 20158234HCID 20158234, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 176Acetic AcidSolvent

Procedure

Ethyl 1H-pyrrolo[2,3-c]pyridine-2-carboxylate (4.225 g, 22.21 mmol) was dissolved in acetic acid (150 mL) and 5% Rh/Al2O3 (9.144 g, 0.2 eq.) was added. The suspension was hydrogenated (45 Bars) at rt for 4 days then at 50° C. for 7 days. The catalyst was removed by filtration through a Celite pad, was washed with acetic acid and the filtrate was evaporated. The residue was dissolved in DCM, washed with saturated aqueous solution of NaHCO3 and aqueous phases were extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give the title compound (4.183 g, 97%). HPLC purity: 92%. M+(LC-MS (ESI)): 195, M−(LC-MS (ESI)): 193

Workup

  1. customat rt
  2. customfor 4 days
  3. customThe catalyst was removed by filtration through a Celite pad
  4. washwas washed with acetic acid
  5. customthe filtrate was evaporated
  6. dissolutionThe residue was dissolved in DCM
  7. washwashed with saturated aqueous solution of NaHCO3 and aqueous phases
  8. extractionwere extracted with DCM
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-7feeb1bbe6c143e4b92c42dadc3764a6
Source dataset
uspto-grants-2011_04
Patent number
US07932389B2

Reaction notes

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