Dimethylformamide → HCID 86583087, compound

HRID 1253457Notes

Reaction equation

HRID 1253457 reaction equation
P(Cl)(Cl)(Cl)=O.CN([CH:9]=[O:10])C.[Br:11][C:12]1[CH:13]=[C:14]([O:21][CH3:22])[C:15]2[N:16]([N:18]=[CH:19][CH:20]=2)[CH:17]=1>>[Br:11][C:12]1[CH:13]=[C:14]([O:21][CH3:22])[C:15]2[N:16]([N:18]=[CH:19][C:20]=2[CH:9]=[O:10])[CH:17]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 446228256-Bromo-4-methoxypyrazolo[1,5-a]pyridine

Product 1

HCID 86583087HCID 86583087, compound

Procedure

Phosphorous oxychloride (513 μl, 5.51 mmol) was added to DMF (8.52 ml, 110 mmol) at 0° C. The bath was removed and the solution was allowed the solution to warm to ambient temperature. After 30 minutes, 6-bromo-4-methoxypyrazolo[1,5-a]pyridine (500 mg, 2.202 mmol) was added, and the mixture was allowed to stir at ambient temperature. After 3.5 h, the reaction was quenched by the addition of saturated aqueous sodium bicarbonate (30 mL) and stirred for 60 minutes. The reaction mixture was diluted in ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and brine then dried over sodium sulfate, filtered and concentrated. The solid was placed under vacuum overnight to remove excess DMF and afford 6-bromo-4-methoxypyrazolo[1,5-a]pyridine-3-carbaldehyde contaminated with about 9% of the starting material.

Workup

  1. customThe bath was removed
  2. waitAfter 3.5 h
  3. customthe reaction was quenched by the addition of saturated aqueous sodium bicarbonate (30 mL)
  4. stirringstirred for 60 minutes
  5. additionThe reaction mixture was diluted in ethyl acetate
  6. washwashed with saturated aqueous sodium hydrogen carbonate and brine
  7. dry with materialthen dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customwas placed under vacuum overnight
  11. customto remove excess DMF

Sources & evidence

ORD record
ord-2c102436a0524ab2b6aeae14089ca149
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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