Sulfuric Acid → HCID 66999313, compound

HRID 2102418Notes

Reaction equation

HRID 2102418 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:9]([F:19])[C:8]([Cl:20])=[C:7]([C:21]#[C:22][Si](C)(C)C)[N:6]=1)=[O:4].[OH:27]S(O)(=O)=O>CC(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:9]([F:19])[C:8]([Cl:20])=[C:7]([C:21](=[O:27])[CH3:22])[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 69005612HCID 69005612, compound

Product 1

HCID 66999313HCID 66999313, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A mixture of 5-chloro-4-fluoro-3-(2-fluorophenylamino)-6-trimethylsilanylethynyl-pyridine-2-carboxylic acid methyl ester (1.00 equivalent), HgSO4 (1.00 equivalent), and conc. H2SO4 (2.00 equivalents) in acetone-water is refluxed with stirring for 3 hours. The reaction mixture is concentrated in vacuo, diluted with EtOAc, and washed with water and brine. The organic layer is dried over MgSO4, filtered, and concentrated in vauco to give the crude material that is purified by trituration or flash column chromatography to afford the desired product as necessary.

Workup

  1. temperatureis refluxed
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. additiondiluted with EtOAc
  4. washwashed with water and brine
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vauco
  8. customto give the crude material that
  9. customis purified by trituration or flash column chromatography

Sources & evidence

ORD record
ord-68d8272c55964889a1e2f7d974ad832a
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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