Potassium Bicarbonate → 5-Bromo-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde

HRID 1475956Notes

Reaction equation

HRID 1475956 reaction equation
[Cl-].[Br:2][C:3]1[CH:8]=[CH:7][N:6]2[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:11]([CH:12]=[N+](C)C)=[C:5]2[CH:4]=1.C(=O)(O)[O-:25].[K+]>CO>[Br:2][C:3]1[CH:8]=[CH:7][N:6]2[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:11]([CH:12]=[O:25])=[C:5]2[CH:4]=1

Participants

4

Reactant 2

HCID 516893Potassium BicarbonateHCID 68276032N-((5-bromo-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)methylene)-N-methylmethanaminium chloride

Product 1

HCID 867112215-Bromo-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridine-3-carbaldehydeYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N-((5-bromo-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)methylene)-N-methylmethanaminium chloride (260 mg, 0.66 mmol) in methanol (3 mL) was added a 3% solution of potassium bicarbonate (3.1 mL) and the mixture was stirred at room temperature for 2 h. The solids were collected by filtration and dried under reduced pressure to afford the title compound as a solid (201 mg, 92%). LCMS m/z 331.0, 333.0 (M+H)+, ret. time=2.13 min.

Workup

  1. filtrationThe solids were collected by filtration
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-611372a62bbe44f5bf2dd2c5db82535f
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

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