Ethyl chloroformate → ethyl 6-chloro-3-oxo-2,3-dihydro-1H-pyrazolo[4,3-c]pyridine-1-carboxylate

HRID 588080Notes

Reaction equation

HRID 588080 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8](=[O:11])[NH:9][NH:10][C:4]=2[CH:3]=1.Cl[C:13]([O:15][CH2:16][CH3:17])=[O:14]>N1C=CC=CC=1.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8](=[O:11])[NH:9][N:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 1182717496-Chloro-1H-pyrazolo[4,3-c]pyridin-3-ol

Product 1

HCID 118271775ethyl 6-chloro-3-oxo-2,3-dihydro-1H-pyrazolo[4,3-c]pyridine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 6-chloro-1H-pyrazolo[4,3-c]pyridin-3(2H)-one (2.64 g, 15.57 mmol) in pyridine (10 mL) and water (14 mL) was added ethyl chloroformate (3.38 g, 31.1 mmol) drop-wise at 0° C. The reaction was removed from the ice bath and was stirred at room temperature overnight. The reaction mixture was filtered and the solid rinsed with water to afford ethyl 6-chloro-3-oxo-2,3-dihydro-1H-pyrazolo[4,3-c]pyridine-1-carboxylate, which was carried onto the next step without further purification. MS ESI calc'd. for C9H8ClN3O3 [M+1]+242. found 242.

Workup

  1. customThe reaction was removed from the ice bath
  2. filtrationThe reaction mixture was filtered
  3. washthe solid rinsed with water

Sources & evidence

ORD record
ord-d70c4d0d22e64f42ac7918dc1edd311f
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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