Cesium carbonate → HCID 67074086, compound

HRID 1852397Notes

Reaction equation

HRID 1852397 reaction equation
F[C:2]1[C:3]([N+:18]([O-:20])=[O:19])=[C:4]([CH:14]=[C:15]([F:17])[CH:16]=1)[NH:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:7]=1[F:13].[NH2:21][C:22]1[CH:23]=[C:24]([OH:29])[CH:25]=[CH:26][C:27]=1[F:28].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[NH2:21][C:22]1[CH:23]=[C:24]([CH:25]=[CH:26][C:27]=1[F:28])[O:29][C:2]1[C:3]([N+:18]([O-:20])=[O:19])=[C:4]([CH:14]=[C:15]([F:17])[CH:16]=1)[NH:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:7]=1[F:13]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 135191803-Amino-4-fluorophenolHCID 57625029HCID 57625029, compound2×

Product 1

HCID 67074086HCID 67074086, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g of 3,5-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline (Intermediate 1A; 2.537 mmol, 1 eq.), 194 mg 3-amino-4-fluorophenol (1.522 mmol, 0.6 eq.) and 1.240 g caesium carbonate (3.806 mmol, 1.5 eq.) were suspended in 12 mL DMF and stirred at rt for 72 h. The reaction mixture was partitioned between butan-2-one and half saturated brine. The layers were separated and the aqueous layer was reextracted twice with ethyl butan-2-one. The combined organic layers were washed with brine, dried, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (n-hexane/ethyl acetate gradient) providing 450 mg of a mixture of the desired product with its para regioisomer that eluted with the same retention time (63% UV purity). This material was used without further purification.

Workup

  1. customThe reaction mixture was partitioned between butan-2-one and half saturated brine
  2. customThe layers were separated
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash column chromatography (n-hexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-6bc96d3cebd544db805432e503aec7ad
Source dataset
uspto-grants-2015_02
Patent number
US08962606B2

Reaction notes

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