Cesium carbonate → 3-Fluoro-4-(6-ethanesulfonyl-pyridin-3-yloxy)-phenylamine

HRID 13306Notes

Reaction equation

HRID 13306 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:19][C:20]1[CH:21]=[C:22]([NH:27]C(=O)OC(C)(C)C)[CH:23]=[CH:24][C:25]=1[OH:26]>CN(C)C=O>[F:19][C:20]1[CH:21]=[C:22]([NH2:27])[CH:23]=[CH:24][C:25]=1[O:26][C:2]1[CH:7]=[N:6][C:5]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11708410tert-Butyl (3-Fluoro-4-hydroxyphenyl)carbamateHCID 231451535-Chloro-2-(ethanesulfonyl)pyridine

Product 1

HCID 231456053-Fluoro-4-(6-ethanesulfonyl-pyridin-3-yloxy)-phenylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

10.9 g of 5-chloro-2-ethanesulfonyl-pyridine and 1.6 g of cesium carbonate were added to a dimethylformamide (150 ml) solution of 10.0 g of tert-butyl (3-fluoro-4-hydroxy-phenyl)-carbamate obtained in Example 196 (step 1), and the reaction liquid was stirred at 100° C. for 3 hours. The solvent was evaporated away under reduced pressure, diluted with chloroform, washed with aqueous saturated sodium bicarbonate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/9) to obtain a crude product. The resulting crude product was dissolved in 4 N hydrochloric acid/dioxane, and stirred at room temperature for 1 hour. The solvent was evaporated away under reduced pressure, diluted with chloroform, washed with water, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/9) to obtain the entitled compound.

Workup

  1. customthe reaction liquid
  2. customThe solvent was evaporated away under reduced pressure
  3. additiondiluted with chloroform
  4. washwashed with aqueous saturated sodium bicarbonate
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was evaporated away under reduced pressure
  7. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/9)

Sources & evidence

ORD record
ord-e093a28fd6504ba3a5bf56ac74fff395
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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