Pyridine → 932705-76-5

HRID 1171077Notes

Reaction equation

HRID 1171077 reaction equation
[CH3:1][C:2]1[CH:7]=CC(S(Cl)(=O)=O)=C[CH:3]=1.N1C=CC=CC=1.[Cl:18][C:19]1[N:27]=[C:26]([Cl:28])[C:25]([F:29])=[CH:24][C:20]=1[C:21]([OH:23])=[O:22].C(=O)([O-])O.[Na+]>C(O)(C)(C)C>[Cl:18][C:19]1[N:27]=[C:26]([Cl:28])[C:25]([F:29])=[CH:24][C:20]=1[C:21]([O:23][C:2]([CH3:7])([CH3:3])[CH3:1])=[O:22]

Participants

6

Reactant 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 27336592,6-Dichloro-5-fluoronicotinic acid

Product 1

HCID 59585008932705-76-5Yield 95%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

P-toluenesulfonyl chloride (53.5 g) was added to a pyridine (100 ml)/tert-butanol (300 ml) solution of 2,6-dichloro-5-fluoronicotinic acid (24.5 g), and stirred overnight at room temperature. The reaction liquid was poured into aqueous 10% sodium hydrogencarbonate solution, stirred at room temperature for 2 hours, and then extracted with ethyl acetate. The extract was washed with saturated saline water, dried with anhydrous magnesium sulfate, the solvent was evaporated off, the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to obtain the entitled compound (29.5 g).

Workup

  1. customThe reaction liquid
  2. stirringstirred at room temperature for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated saline water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated off
  7. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-89934113a8514638aff28380d1b27ea1
Source dataset
uspto-grants-2010_11
Patent number
US07829586B2

Reaction notes

Loading…