Chlorosuccinimide → HCID 178505546, compound

HRID 42581

Reaction equation

HRID 42581 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:11]=[C:10]3[NH:27][N:28]=[CH:29][C:9]=23)=[CH:4][CH:3]=1.[Cl:30]N1C(=O)CCC1=O>CN(C=O)C>[Cl:30][C:29]1[C:9]2[C:10](=[N:11][C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[C:13]([C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)[C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[NH:27][N:28]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 119613744,6-Bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 178505546HCID 178505546, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (0.20 g, 0.5 mmol, obtained in example 1) in DMF (5 mL), N-chlorosuccinimide (0.10 g, 0.8 mmol) was added under argon atmosphere and the mixture was heated to 60° C. for 5 h. It was washed with 1 N NaOH and extracted with CHCl3 and EtOAc. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 171 mg of title compound (yield: 79%).

Workup

  1. washIt was washed with 1 N NaOH
  2. extractionextracted with CHCl3 and EtOAc
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe crude product obtained
  6. customwas purified by chromatography on silica gel
  7. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-2fea9ee53f4c42afa65b6d5983f650b4
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Linked notes

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