Water → HCID 68294766, compound

HRID 1854019Notes

Reaction equation

HRID 1854019 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:26]1[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]1.O>CN(C=O)C.C(OCC)(=O)C>[CH:11]([N:8]1[C:6]2[N:7]=[C:2]([O:1][CH:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)[CH:3]=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]=2[CH:10]=[N:9]1)([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 115213614-bromo-1-methylpiperidineHCID 178469345HCID 178469345, compound

Product 1

HCID 68294766HCID 68294766, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 6-hydroxy-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (1 equiv.) was suspended in DMF and K2CO3 (1.5 equiv.) and 4-bromo-1-methylpiperidine (1.5 equiv.) was added to it. The reaction mixture was stirred at room temperature for overnight. On completion of reaction, water was added to it and extraction was carried out using ethyl acetate; the combined organic layers were washed with water, brine and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and residue was purified by silica gel column chromatography to obtain the desired intermediate.

Workup

  1. additionwas added to it and extraction
  2. washthe combined organic layers were washed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customSolvent was removed under reduced pressure and residue
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6717f43f07a84369bd88ea936d2adcf2
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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