HCID 178439493, compound → HCID 178439492, compound

HRID 489373Notes

Reaction equation

HRID 489373 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([CH2:21][CH2:22][CH3:23])[NH:13][C:12]2=[N:24][NH:25][CH:26]=[C:11]12)([O-])=O>CO.[C].[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([CH2:21][CH2:22][CH3:23])[NH:13][C:12]2=[N:24][NH:25][CH:26]=[C:11]12

Participants

4

Reactant 1

HCID 178439493HCID 178439493, compound

Product 1

HCID 178439492HCID 178439492, compoundYield 7.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 4,7-dihydro-4-(2-nitrophenyl)-6-propyl-2H-pyrazolo[3,4-b]pyridine-5-carboxylate (1.68 g) in methanol (30 mL) was added 5% palladium-carbon (500 mg), and the mixture was stirred under 10 atm for 3 hours. After removing palladium-carbon by Celite filtration, the solvent was evaporated under reduced pressure to give an oil. The obtained oil was purified by silica gel column chromatography (eluent:hexane-ethyl acetate (1:1)) to give the title compound (120 mg) as colorless crystals.

Workup

  1. customAfter removing palladium-carbon
  2. filtrationby Celite filtration
  3. customthe solvent was evaporated under reduced pressure
  4. customto give an oil
  5. customThe obtained oil was purified by silica gel column chromatography (eluent:hexane-ethyl acetate (1:1))

Sources & evidence

ORD record
ord-d17b87e7f66941c3b149193f507fdbed
Source dataset
uspto-grants-2005_12
Patent number
US06977262B2

Reaction notes

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