Water → 1H-Pyrazolo[3,4-b]pyridine-4-carboxylic acid, 6-chloro-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-, ethyl ester

HRID 2360677Notes

Reaction equation

HRID 2360677 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:15]([CH3:16])=[N:14][NH:13][C:8]=2[N:9]=[C:10]([Cl:12])[CH:11]=1)=[O:5])[CH3:2].[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:15]([CH3:16])=[N:14][N:13]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][O:17]3)[C:8]=2[N:9]=[C:10]([Cl:12])[CH:11]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 178468964HCID 178468964, compound

Product 1

HCID 866802961H-Pyrazolo[3,4-b]pyridine-4-carboxylic acid, 6-chloro-3-methyl-1-(tetrahydro-2H-pyran-2-yl)-, ethyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-chloro-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester (28.5 g), 3,4-dihydro-2H-pyran (23.7 mL) and p-toluenesulfonic acid monohydrate (6.8 g) in THF (800 mL) was stirred at r.t. until the reaction was complete. The mixture was poured into water (1.5 l) and extracted with ethyle acetate (600 mL). The organic phase was dried over magnesium sulfate and concentrated in a vacuo. The crude product was purified by silica gel chromatography (heptane/ethyl acetate gradient). 37.8 g (98%) of the title compound were obtained.

Workup

  1. extractionextracted with ethyle acetate (600 mL)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated in a vacuo
  4. customThe crude product was purified by silica gel chromatography (heptane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-501e9b7fe1904cb295f41daaff2a5a00
Source dataset
uspto-grants-2014_04
Patent number
US08686150B2

Reaction notes

Loading…