o-Fluorobenzaldehyde → HCID 178488657, compound

HRID 1526111Notes

Reaction equation

HRID 1526111 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][C:11]1[CH:15]=[C:14]([NH2:16])[NH:13][N:12]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=O)[CH2:26][C:27]#[N:28])=[CH:21][CH:20]=1>C(#N)C>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:26]([C:27]#[N:28])=[C:25]([C:22]2[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=2)[NH:16][C:14]2[NH:13][N:12]=[C:11]([CH3:10])[C:15]1=2

Participants

5

Reactant 3

HCID 67970o-FluorobenzaldehydeHCID 2333984-MethoxybenzoylacetonitrileHCID 178418690HCID 178418690, compound

Product 1

HCID 178488657HCID 178488657, compoundYield 241.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.5 ml (14.27 mmol) of 2-fluorobenzaldehyde and 1.66 g (5.18 mmol) of 3-methyl-1H-pyrazol-5-amine are added respectively to a solution of 2.5 g (14.27 mmol) of 3-(4-methoxyphenyl)-3-oxopropanenitrile in 60 ml of acetonitrile. The reaction mixture is carried at reflux for 16 hours. The solution is allowed to return to room temperature and then the solid is filtered and rinsed several times with acetonitrile to yield 4.5 g (87%) of 4-(2-fluorophenyl)-6-(4-methoxyphenyl)-3-methyl-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile in the form of a white solid.

Workup

  1. temperatureat reflux for 16 hours
  2. customto return to room temperature
  3. filtrationthe solid is filtered
  4. washrinsed several times with acetonitrile

Sources & evidence

ORD record
ord-d6a6c29578c646ab94e4df6d49c7391c
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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