Ammonia → 2-(1-methylcyclopropyl)-1H-pyrrolo[2,3-c]pyridin-5-amine

HRID 513082Notes

Reaction equation

HRID 513082 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]3([CH3:14])[CH2:13][CH2:12]3)[NH:8][C:5]2=[CH:6][N:7]=1.[NH3:15]>CCO>[CH3:14][C:11]1([C:9]2[NH:8][C:5]3=[CH:6][N:7]=[C:2]([NH2:15])[CH:3]=[C:4]3[CH:10]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 579081755-chloro-2-(1-methylcyclopropyl)-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 579081672-(1-methylcyclopropyl)-1H-pyrrolo[2,3-c]pyridin-5-amineYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 100 mL autoclave, a solution of 5-chloro-2-(1-methylcyclopropyl)-1H-pyrrolo[2,3-c]pyridine (1.0 g, 4.9 mmol) and CuSO4.5H2O (100 mg, 0.4 mmol) in aqueous ammonia (60 mL) and EtOH (20 mL) was heated to 200° C. and stirred at this temperature for 8 hours. The mixture was allowed to cool down to room temperature. The alcohol was removed under vacuum. The resulting mixture was extracted with ethyl acetate (50 mL×3). The combined organic layer was dried over anhydrous Na2SO4 and purified by chromatography on silica gel (2% CH3OH in dichloromethane as eluant) to afford 2-(1-methylcyclopropyl)-1H-pyrrolo[2,3-c]pyridin-5-amine (250 mg, 27%). 1H-NMR (DMSO, 300 MHz) δ 7.96 (s, 1H), 6.37 (s, 1H), 5.88 (d, J=1.2, 1H), 5.01 (br s, 2H), 1.41 (s, 3H), 0.98 (t, J=2.1, 2H), 0.80 (t, J=2.1, 2H).

Workup

  1. customThe alcohol was removed under vacuum
  2. extractionThe resulting mixture was extracted with ethyl acetate (50 mL×3)
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. custompurified by chromatography on silica gel (2% CH3OH in dichloromethane as eluant)

Sources & evidence

ORD record
ord-45c117a43e7e4ace9ffb930e7e1b106a
Source dataset
uspto-grants-2015_08
Patent number
US09102672B2

Reaction notes

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