Pyridine → HCID 86703405, compound

HRID 1501532Notes

Reaction equation

HRID 1501532 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C:17]1[CH:18]=[C:19]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:20]2[CH:25]=[N:24][N:23]([CH:26]([CH3:28])[CH3:27])[C:21]=2[N:22]=1.N1C=CC=CC=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:26]([N:23]1[C:21]2[N:22]=[C:17]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:18]=[C:19]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:20]=2[CH:25]=[N:24]1)([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 178469345HCID 178469345, compound

Product 1

HCID 86703405HCID 86703405, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoromethanesulfonic anhydride (5.23 g, 18.5 mmol) was added to a cooled solution of ethyl 6-hydroxy-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (4.2 g, 16.9 mmol) and pyridine (1.46 g, 18.5 mmol) in DCM (60 mL); and it was allowed to stirred at room temperature for 2 h. After completion of the reaction, saturated NaHCO3 solution (60 mL) was added to it and extraction was carried out using DCM (30 mL×3). The combined organic layers were washed with water (100 mL); brine (100 mL); dried over anhydrous Na2SO4; filtered and concentrated under reduced pressure. The residue was finally purified by silica gel column chromatography to provide pure the desired intermediate (5 g, 77.8% yield).

Workup

  1. additionwas added to it and extraction
  2. washThe combined organic layers were washed with water (100 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was finally purified by silica gel column chromatography

Sources & evidence

ORD record
ord-205b925480f54ef9a78dea326e5f562a
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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