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

HRID 513071Notes

Reaction equation

HRID 513071 reaction equation
[C:1]([C:5]1[NH:14][C:8]2=[CH:9][N:10]=[C:11](Cl)[CH:12]=[C:7]2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH3:15].O>>[C:1]([C:5]1[NH:14][C:8]2=[CH:9][N:10]=[C:11]([NH2:15])[CH:12]=[C:7]2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 12896473Azane;hydrateHCID 579081512-tert-butyl-5-chloro-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 579081612-tert-butyl-1H-pyrrolo[2,3-c]pyridin-5-amineYield 27%

Conditions

Temperature
200 °C

Procedure

To a solution of 2-tert-butyl-5-chloro-1H-pyrrolo[2,3-c]pyridine (5.0 g, 24 mmol) in NH3.H2O (400 mL) was added CuSO4.5H2O (595 mg, 2.39 mmol). The mixture was heated at 200° C. (3 MPa pressure) for 24 h. After cooling, the mixture was extracted with CH2Cl2 (150 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure to give a residue, which was purified by column (petroleum ether/ethyl acetate=10/1) to obtain 2-tert-butyl-1H-pyrrolo[2,3-c]pyridin-5-amine (1.2 g, 27%). 1H NMR (400 MHz, DMSO) δ 10.66 (br s, 1H), 8.02 (s, 1H), 6.39 (s, 1H), 5.86 (d, J=1.2 Hz, 1H), 4.85 (br s, 2H), 1.29 (s, 9H).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with CH2Cl2 (150 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. customevaporated under reduced pressure
  5. customto give a residue, which
  6. customwas purified by column (petroleum ether/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-6a62b768266b440489931a62a2e3a88f
Source dataset
uspto-grants-2015_08
Patent number
US09102672B2

Reaction notes

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