Chlorosuccinimide → Ethyl (3-chloro-2H-pyrazolo[3,4-b]pyridin-2-yl)acetate

HRID 930566Notes

Reaction equation

HRID 930566 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][N:6]1[CH:14]=[C:13]2[C:8]([N:9]=[CH:10][CH:11]=[CH:12]2)=[N:7]1)[CH3:2].C1C(=O)N([Cl:23])C(=O)C1>ClCCl>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][N:6]1[C:14]([Cl:23])=[C:13]2[C:8]([N:9]=[CH:10][CH:11]=[CH:12]2)=[N:7]1)[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 57642783Ethyl (2H-pyrazolo[3,4-b]pyridin-2-yl)acetate

Product 1

HCID 57642771Ethyl (3-chloro-2H-pyrazolo[3,4-b]pyridin-2-yl)acetateYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of pyrazolo[3,4-b]pyridin-2-yl-acetic acid ethyl ester 57 (40.2 mg, 0.2 mmol, 1 equiv) in 1 mL of dichloromethane was added NCS (32.7 mg, 1.2 mmol, 1.2 equiv). The resultant mixture was heated at 70° C. for 30 min., cooled to room temperature, and diluted with 100 mL of dichloromethane. The organic solution was washed with 50 mL of saturated sodium bicarbonate aqueous solution, and 50 mL of brine. The organic layer was separated and dried over sodium sulfate. Evaporation of solvent in vacuo gave 46.7 mg of (3-chloro-pyrazolo[3,4-b]pyridin-2-yl)-acetic acid ethyl ester as yellow solid.

Workup

  1. washThe organic solution was washed with 50 mL of saturated sodium bicarbonate aqueous solution, and 50 mL of brine
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of solvent in vacuo

Sources & evidence

ORD record
ord-616c86efbc5744769072184be5684e59
Source dataset
uspto-grants-2016_03
Patent number
US09296740B2

Reaction notes

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