Chlorosuccinimide → 6-Bromo-3-chloro-4-methoxypyrazolo[1,5-a]pyridine

HRID 1253456Notes

Reaction equation

HRID 1253456 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]2[N:6]([N:8]=[CH:9][CH:10]=2)[CH:7]=1.[Cl:13]N1C(=O)CCC1=O>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]2[N:6]([N:8]=[CH:9][C:10]=2[Cl:13])[CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 446228256-Bromo-4-methoxypyrazolo[1,5-a]pyridine

Product 1

HCID 672072806-Bromo-3-chloro-4-methoxypyrazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-bromo-4-methoxypyrazolo[1,5-a]pyridine (1010 mg, 4.43 mmol) in acetonitrile (40 ml) was added N-chlorosuccinimide (1180 mg, 8.86 mmol). The reaction mixture was stirred at room temperature for 6 hours. The reaction mixture was partitioned between dichloromethane (100 ml) and 1N aqueous sodium hydroxide (100 ml). The organic layer was washed with brine (100 ml). The organic layer was dried over sodium sulfate, filtered and concentrated to afford 6-bromo-3-chloro-4-methoxypyrazolo[1,5-a]pyridine as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 8.66 (s, 1H); 8.03 (s, 1H); 6.84 (s, 1H); 3.94 (s, 1H). LRMS (ESI) calculated for C8H6BrClN2O [M+H]+, 260.9; found 261.0.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane (100 ml) and 1N aqueous sodium hydroxide (100 ml)
  2. washThe organic layer was washed with brine (100 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-919f76a87d674e6b952a82971b1d3693
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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