N-bromobutanimide → HCID 11772769, compound

HRID 1354172Notes

Reaction equation

HRID 1354172 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:20](C(O)=O)=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:19])([F:18])[F:17])=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C([O-])(O)=O.[Na+].C1C(=O)N([Br:36])C(=O)C1>CN(C=O)C.O>[Br:36][C:20]1[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[N:9][N:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=12

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 17924715HCID 17924715, compound

Product 1

HCID 11772769HCID 11772769, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-fluoro-phenyl)-6-trifluoromethyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid (403 mg, 1.24 mmol) and NaHCO3 (355 mg, 3.4 eq) in DMF (10 ml) was added NBS (1.1 eq, 244 mg) and the resulting solution stirred at rt for 1.5 h. The mixture was diluted with water and extracted with ethyl acetate (3×10 ml). The combined organic phases were washed with water (3×10 ml), dried and concentrated in vacuo to give the title compound as a brown solid (390 mg, 85%). MH+ 358/359

Workup

  1. extractionextracted with ethyl acetate (3×10 ml)
  2. washThe combined organic phases were washed with water (3×10 ml)
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-074345c5ad534b48bc207beb20d2d65c
Source dataset
uspto-grants-2007_05
Patent number
US07223772B1

Reaction notes

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