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

HRID 588091Notes

Reaction equation

HRID 588091 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8](=[O:16])[NH:9][N:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>CN(C=O)C>[CH2:23]([N:9]1[C:8](=[O:16])[C:5]2[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][C:4]=2[N:10]1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 118271775ethyl 6-chloro-3-oxo-2,3-dihydro-1H-pyrazolo[4,3-c]pyridine-1-carboxylate2×

Product 1

HCID 118271800ethyl 2-benzyl-6-chloro-3-oxo-2,3-dihydro-1H-pyrazolo[4,3-c]pyridine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 6-chloro-3-oxo-2,3-dihydro-1H-pyrazolo[4,3-c]pyridine-1-carboxylate (Intermediate 1B; 582 mg, 2.41 mmol), potassium carbonate (666 mg, 4.82 mmol), and benzyl bromide (0.345 mL, 2.9 mmol) were stirred in DMF (10 mL) at room temperature for 16 h. Water was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by flash chromatography (6-50% EtOAc-hexanes) gave ethyl 2-benzyl-6-chloro-3-oxo-2,3-dihydro-1H-pyrazolo[4,3-c]pyridine-1-carboxylate. MS ESI calc'd. for C16H14ClN3O3 [M+1]+ 332. found 332. Ethyl 3-(benzyloxy)-6-chloro-1H-pyrazdo[4,3-c]pyridine-1-carboxylate was also obtained. MS ESI calc'd. for C16H14ClN3O3 [M+1]+ 332. found 332.

Workup

  1. extractionthe products extracted into EtOAc (×2)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash chromatography (6-50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-a65c33a870ce47ddb0c0bbdff12ee6da
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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