Trifluoroacetic acid → HCID 59519392, compound

HRID 1161825Notes

Reaction equation

HRID 1161825 reaction equation
[F:1][C:2]1[C:3]2[C:4](=[C:20]([CH3:23])[O:21][N:22]=2)[N:5]=[C:6]([C:16]([O:18][CH3:19])=[O:17])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15].[I:24]N1C(=O)CCC1=O.C(O)(C(F)(F)F)=O>CN(C=O)C>[F:1][C:2]1[C:3]2[C:4](=[C:20]([CH3:23])[O:21][N:22]=2)[N:5]=[C:6]([C:16]([O:18][CH3:19])=[O:17])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([I:24])=[CH:11][C:10]=1[F:15]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 59519478HCID 59519478, compound

Product 1

HCID 59519392HCID 59519392, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of methyl 7-fluoro-6-(2-fluorophenylamino)-3-methylisoxazolo[4,3-b]pyridine-5-carboxylate (1.35 g, 4.25 mmol) in DMF (40 ml) is added N-iodosuccinimide (1.43 g, 6.37 mmol) and TFA (2.5 ml). After stirring at room temperature for 4 h, the reaction is quenched with saturated aqueous NH4Cl solution (100 ml) and extracted with EtOAc (2×100 ml). The combined organic solution is washed with brine (100 ml), dried over MgSO4 and concentrated. Silica gel chromatography yields the title compound.

Workup

  1. customthe reaction is quenched with saturated aqueous NH4Cl solution (100 ml)
  2. extractionextracted with EtOAc (2×100 ml)
  3. washThe combined organic solution is washed with brine (100 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f10763b1d584c559a239b620e08804e
Source dataset
uspto-grants-2010_10
Patent number
US07820664B2

Reaction notes

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