Ethanol → 1-(4-Fluorobenzyl)-5-methanesulfonyl-2-(5-methyl-[1,2,4]oxadiazol-3-yl)indole

HRID 1432255ノート

反応式

HRID 1432255 の反応式
[C:1]([C:3]1[N:4]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][CH:6]=2)#[N:2].Cl.[NH2:25]O.[OH-].[K+].[CH2:29]([OH:31])[CH3:30]>>[F:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][N:4]2[C:5]3[C:10](=[CH:9][C:8]([S:12]([CH3:15])(=[O:13])=[O:14])=[CH:7][CH:6]=3)[CH:11]=[C:3]2[C:1]2[N:25]=[C:29]([CH3:30])[O:31][N:2]=2)=[CH:22][CH:21]=1

参加物

5

反応物 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 225044482-Cyano-1-(4-fluorobenzyl)-5-methanesulfonylindole

生成物 1

HCID 225044061-(4-Fluorobenzyl)-5-methanesulfonyl-2-(5-methyl-[1,2,4]oxadiazol-3-yl)indole

反応条件

温度
100 °C

実験手順

A mixture of the compound obtained in Example 24 (1) (68 mg), hydroxylamine hydrochloride (22 mg), potassium hydroxide (18 mg) and ethanol (1 ml) was heated under reflux for 2 hours. After the insolubles were filtered off, the reaction mixture was concentrated under reduced pressure. A mixture of the resulting residue and dimethylacetamide dimethylacetal (1-ml) was stirred at 100° C. for 1 hour. Water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane ethyl acetate=1:1) to obtain 50 mg of the desired product as a white crystal.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. filtrationAfter the insolubles were filtered off
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. additionA mixture of the resulting residue and dimethylacetamide dimethylacetal (1-ml)
  6. additionWater was added
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with water
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-0d0b21f2d3ef4d00b79257998f486f15
出典データセット
uspto-grants-2009_11
特許番号
US07612070B2

反応ノート

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