N-bromobutanimide → 3-bromo-6-(1-tert-butyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-4-ol

HRID 2209237Notes

Reaction equation

HRID 2209237 reaction equation
[C:1]([N:5]1[CH:9]=[C:8]([C:10]2[CH:11]=[C:12]([OH:19])[C:13]3[N:14]([N:16]=[CH:17][CH:18]=3)[CH:15]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[Br:20]N1C(=O)CCC1=O>C(#N)C.ClCCl>[Br:20][C:18]1[CH:17]=[N:16][N:14]2[CH:15]=[C:10]([C:8]3[CH:7]=[N:6][N:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:9]=3)[CH:11]=[C:12]([OH:19])[C:13]=12

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1178428446-(1-tert-butyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-4-ol

Product 1

HCID 1178429823-bromo-6-(1-tert-butyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-4-ol

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(1-tert-butyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-4-ol (138 mg, 0.538 mmol) in acetonitrile (6 mL) was added N-bromosuccinimide (105 mg, 0.590 mmol). The solution was stirred at room temperature for 1 h. The reaction was diluted with dichloromethane, washed with water and 2N NaOH. The combined aqueous layers were neutralized and extracted with ethyl acetate. The combined organic layers were washed with brine, dried, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford 3-bromo-6-(1-tert-butyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-4-ol.

Workup

  1. washwashed with water and 2N NaOH
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-b7c9891486b94a858b91f6cf1a69b97a
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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