Trifluoroacetic acid → Methyl 5-acetyl-2-(2-fluoro-4-iodophenylamino)-3,4-difluorobenzoate

HRID 558246Notes

Reaction equation

HRID 558246 reaction equation
[C:1]([C:4]1[C:5]([F:23])=[C:6]([F:22])[C:7]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2].C1C(=O)N([I:31])C(=O)C1.C(O)(C(F)(F)F)=O>CN(C=O)C.CCOC(C)=O>[C:1]([C:4]1[C:5]([F:23])=[C:6]([F:22])[C:7]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([I:31])=[CH:17][C:16]=2[F:21])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 59519431Methyl 5-acetyl-2-(2-fluorophenylamino)-3,4-difluorobenzoate

Product 1

HCID 59519381Methyl 5-acetyl-2-(2-fluoro-4-iodophenylamino)-3,4-difluorobenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 5-acetyl-2-(2-fluorophenylamino)-3,4-difluorobenzoate (0.47 mmol, 0.16 g) in DMF (10 ml) was added NIS (0.56 mmol, 0.13 g) and TFA (0.10 ml), and the reaction was stifled at room temp overnight. The crude was diluted with EtOAc and washed with H2O. The organic fraction was dried over MgSO4 and concentrated under reduced pressure to yield the desired product in 90% (0.23 g).

Workup

  1. washwashed with H2O
  2. dry with materialThe organic fraction was dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e807b901fb0a4356a8cf7ddd48731e63
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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