Azane;hydrate → 2-ethyl-1H-pyrrolo[2,3-c]pyridin-5-amine

HRID 1044011Notes

Reaction equation

HRID 1044011 reaction equation
[CH2:1]([C:3]1[NH:12][C:6]2=[CH:7][N:8]=[C:9](Cl)[CH:10]=[C:5]2[CH:4]=1)[CH3:2].[NH3:13].O>CCO>[CH2:1]([C:3]1[NH:12][C:6]2=[CH:7][N:8]=[C:9]([NH2:13])[CH:10]=[C:5]2[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 12896473Azane;hydrateHCID 579081942-ethyl-5-chloro-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 579081832-ethyl-1H-pyrrolo[2,3-c]pyridin-5-amineYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

A suspension of 2-ethyl-5-chloro-1H-pyrrolo[2,3-c]pyridine (1.3 g, 7.19 mmol) in EtOH (20 mL), CuSO4.5H2O (179 mg, 0.72 mmol) and NH3—H2O (60 ml) was added into an autoclave (100 mL). The reaction was stirred at 200° C. and 2 MPa for 10 h. The reaction was cooled to 25° C. and was quenched with water and extracted with ethyl acetate (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10/1) to give 2-ethyl-1H-pyrrolo[2,3-c]pyridin-5-amine (190 mg, 16%). 1H-NMR (CDCl3, 300 MHz) δ 10.71 (brs, H), 8.00 (s, 1H), 6.39 (s, 1H), 5.87 (s, 1H), 4.89 (br s, 2H), 2.65 (q, J=7.5 Hz, 2H), 1.22 (t, J=7.5 Hz, 3H).

Workup

  1. additionwas added into an autoclave (100 mL)
  2. temperatureThe reaction was cooled to 25° C.
  3. customwas quenched with water
  4. extractionextracted with ethyl acetate (100 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10/1)

Sources & evidence

ORD record
ord-493363d370254d09b9312bd681f61d3f
Source dataset
uspto-grants-2013_10
Patent number
US08563573B2

Reaction notes

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