HCID 178488657, compound → HCID 178488913, compound

HRID 1526112Notes

Reaction equation

HRID 1526112 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]#[N:15])=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[NH:11][C:10]2[NH:24][N:25]=[C:26]([CH3:27])[C:9]1=2>ClCCl.CO.[O-2].[Mn+2]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([C:14]#[N:15])=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:11]=[C:10]2[NH:24][N:25]=[C:26]([CH3:27])[C:9]=12

Participants

5

Reactant 1

HCID 178488657HCID 178488657, compound

Product 1

HCID 178488913HCID 178488913, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 160959Manganese oxideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

5.43 g (62.4 mmol) of manganese oxide is added to 4.5 g (12.49 mmol) of 4-(2-fluorophenyl)-6-(4-methoxyphenyl)-3-methyl-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile in solution in 60 ml of dichloromethane and 15 ml of methanol. The reaction mixture is placed in an ultrasonic bath for 5 minutes and then stirred at room temperature for 20 hours before being filtered on Dicalite. The filtrate is evaporated to yield 4.1 g (92%) of 4-(2-fluorophenyl)-6-(4-methoxyphenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile in the form of a yellow solid.

Workup

  1. filtrationbefore being filtered on Dicalite
  2. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-304a2e94b8da42bfa83c0a4161078aee
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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