Cesium carbonate → HCID 67074413, compound

HRID 1852390Notes

Reaction equation

HRID 1852390 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[C:23]([CH3:29])=[C:24]([OH:28])[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[NH2:21][C:22]1[C:23]([CH3:29])=[C:24]([CH:25]=[CH:26][CH:27]=1)[O:28][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

6

Reactant 3

HCID 10796Cesium carbonateHCID 1044482-Amino-o-cresolHCID 57625029HCID 57625029, compound2×

Product 1

HCID 67074413HCID 67074413, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.6 g of 3,5-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline (Intermediate 1A; 9.2 mmol, 1 eq.), 1.1 g 3-amino-2-methyl phenol (9.2 mmol, 1 eq.) and 4.5 g caesium carbonate (13.8 mmol, 1.5 eq.) were suspended in 35 mL DMF and stirred at rt for 16 h. LCMS analysis showed complete turnover. The reaction mixture was diluted with ethyl acetate, quenched with saturated sodium chloride solution, the layers were separated and the aqueous layer was reextracted with ethyl acetate. The combined organic layers were dried, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (n-hexane/ethyl acetate gradient) providing 1.18 of the desired product (26% yield).

Workup

  1. customquenched with saturated sodium chloride solution
  2. customthe layers were separated
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography (n-hexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-9c8b9aa5263d4f5e81080555bebcddff
Source dataset
uspto-grants-2015_02
Patent number
US08962606B2

Reaction notes

Loading…