HCID 86598643, compound → HCID 86598644, compound

HRID 500578Notes

Reaction equation

HRID 500578 reaction equation
[CH3:1][Mg+].[Br-].[CH3:4][O:5][C:6](=[O:29])[C:7]1[CH:12]=[C:11]([C:13](=[O:15])[CH3:14])[C:10]([NH:16][CH:17]=[O:18])=[C:9]([F:19])[C:8]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=1[F:28]>CCOCC.C1COCC1>[CH3:4][O:5][C:6](=[O:29])[C:7]1[CH:12]=[C:11]([C:13]([OH:15])([CH3:1])[CH3:14])[C:10]([NH:16][CH:17]=[O:18])=[C:9]([F:19])[C:8]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=1[F:28]

Participants

5

Reactant 2

HCID 86598643HCID 86598643, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 86598644HCID 86598644, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of MeMgBr (3.20 equiv., 3.0 M solution in diethyl ether) in ether is added a solution of 5-acetyl-2-(4-bromo-2-fluorophenylamino)-3-fluoro-4-formylamino-benzoic acid methyl ester (1.00 equiv.) in THF at 0° C. The reaction mixture is warmed to room temperature and stirred for 16 hours. The reaction is quenched with saturated aqueous NH4Cl and diluted with EtOAc. The organic layer is washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that is used directly without further purification.

Workup

  1. customThe reaction is quenched with saturated aqueous NH4Cl
  2. additiondiluted with EtOAc
  3. washThe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1242d8f9e9314d06b0a4beab932c2479
Source dataset
uspto-grants-2010_08
Patent number
US07772234B2

Reaction notes

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