Ammonia → 5-Fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide

HRID 1691607

反応式

HRID 1691607 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:6]([C:19]([OH:21])=O)=[CH:5]2.S(Cl)(Cl)=O.[NH3:26]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:6]([C:19]([NH2:26])=[O:21])=[CH:5]2

参加物

5

反応物 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 574315135-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid

生成物 1

HCID 668456965-Fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide収率 29.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A suspension, stirred at 20° C., of 2 g (6.96 mmol) of 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid, prepared according to the protocol described in step 1.1, in 80 ml of dry toluene is admixed with 5.08 ml (69.62 mmol) of thionyl chloride. The reaction mixture is stirred at reflux for 2 hours and then concentrated under reduced pressure. The resulting product is taken up in 10 ml of dichloromethane and this solution is poured dropwise into a solution of 9.12 ml (69.62 mmol) of 30% aqueous ammonia. The reaction mixture is stirred at 20° C. for 14 hours. After this time a solid is recovered by filtration and triturated in 50 ml of diisopropyl ether. Filtration and drying under reduced pressure give 0.58 g of expected product.

後処理

  1. customprepared
  2. temperatureat reflux for 2 hours
  3. concentrationconcentrated under reduced pressure
  4. stirringThe reaction mixture is stirred at 20° C. for 14 hours
  5. filtrationAfter this time a solid is recovered by filtration
  6. customtriturated in 50 ml of diisopropyl ether
  7. filtrationFiltration
  8. customdrying under reduced pressure

出典と根拠

ORDレコード
ord-fa6bd15c00ac4b898eb0f8846c2add89
出典データセット
uspto-grants-2012_04
特許番号
US08153796B2

関連ノート

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