Pyridine → 6,6-Difluoro-5-methyl-5-hexenyl 6-(toluene-4-sulfonylamino)nicotinate

HRID 917370Notes

Reaction equation

HRID 917370 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[CH:25]=[CH:24][C:11]([C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH3:23])=[C:20]([F:22])[F:21])=[O:13])=[CH:10][N:9]=1.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>Cl>[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32]([NH:7][C:8]2[CH:25]=[CH:24][C:11]([C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([CH3:23])=[C:20]([F:22])[F:21])=[O:13])=[CH:10][N:9]=2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 230203546,6-Difluoro-5-methyl-5-hexenyl 6-aminonicotinate

Product 1

HCID 230202826,6-Difluoro-5-methyl-5-hexenyl 6-(toluene-4-sulfonylamino)nicotinateYield 90.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 5 ml of pyridine was dissolved 0.62 g (2.3 mmol) of 6,6-difluoro-5-methyl-5-hexenyl 6-aminonicotinate, followed by the addition of 0.48 g (2.5 mmol) of toluene-4-sulfonylchloride under ice-cooling, stirring for 10 minutes and then stirring at room temperature for 15 hours. The reaction liquid was then poured in 5% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 0.88 g (yield: 90%) of 6,6-difluoro-5-methyl-5-hexenyl 6-(toluene-4-sulfonylamino)nicotinate.

Workup

  1. temperaturecooling
  2. stirringstirring at room temperature for 15 hours
  3. customThe reaction liquid
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
  7. customThe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-d9945211f11440aca5ad09f2c632ea28
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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