3-Chloro-2-fluoroaniline → HCID 86707773, compound

HRID 2410119Notes

Reaction equation

HRID 2410119 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:24])[N:9]([CH:21]([CH3:23])[CH3:22])[C:10]=1[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[CH3:20])O)=[O:5])[CH3:2].[Cl:25][C:26]1[C:27]([F:33])=[C:28]([CH:30]=[CH:31][CH:32]=1)[NH2:29]>O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:24])[N:9]([CH:21]([CH3:23])[CH3:22])[C:10]=1[CH:11]([NH:29][C:28]1[CH:30]=[CH:31][CH:32]=[C:26]([Cl:25])[C:27]=1[F:33])[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[CH3:20])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 750143-Chloro-2-fluoroanilineHCID 86707752HCID 86707752, compound

Product 1

HCID 86707773HCID 86707773, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared in analogy to the procedure described for step E2 but using intermediate C and 3-chloro-2-fluoroaniline. The reaction was stirred at rt for 1.5 h. The reaction mixture was diluted with H2O and extracted. The organic layers were washed with a saturated aqueous NaHCO3 solution, dried (Na2SO4), filtered and concentrated. The product was purified by flash chromatography (hexane/EtOAc, 90:1→65:35). The residue was then triturated in CH2Cl2 to give the title compound as white foam. tR: 1.45 min (LC-MS 2); ESI-MS: 542.0/544.0/546.0 [M+H]+ (LC-MS 2).

Workup

  1. customThe title compound was prepared in analogy to the procedure
  2. extractionextracted
  3. washThe organic layers were washed with a saturated aqueous NaHCO3 solution
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by flash chromatography (hexane/EtOAc, 90:1→65:35)
  8. customThe residue was then triturated in CH2Cl2

Sources & evidence

ORD record
ord-8528add2ee7b4863bc92d130e95fa2ef
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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