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

HRID 917370ノート

反応式

HRID 917370 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d9945211f11440aca5ad09f2c632ea28
出典データセット
uspto-grants-2007_09
特許番号
US07273878B2

反応ノート

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