Potassium Iodide → 8-Fluoro-5-(4-fluorophenyl)-2-(5-cyano-1-pentyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1156788ノート

反応式

HRID 1156788 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]3[CH2:18][CH2:19][NH:20][CH2:21][C:5]=3[C:4]=2[CH:3]=1.Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]#[N:29].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].CC(C)C(=O)C>O>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[C:6]3[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]#[N:29])[CH2:21][C:5]=3[C:4]=2[CH:3]=1

参加物

7

反応物 5

HCID 4875Potassium IodideHCID 10340Sodium Carbonate2 回HCID 112513-Methyl-2-butanoneHCID 810936-BromohexanenitrileHCID 126299068-fluoro-5-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

生成物 1

HCID 128552868-Fluoro-5-(4-fluorophenyl)-2-(5-cyano-1-pentyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

8-fluoro-5-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (10.8 g, 0.034 mole), 6-bromohexanenitrile (6.5 g, 0.037 mole), anhydrous sodium carbonate (21.6 g, 0.204 mole), potassium iodide (100 mg) and 3-methyl-2-butanone (250 ml) were combined and the mixture refluxed for 24 hours. The reaction mixture was cooled, diluted with 250 ml of water and stirred to dissolve excess sodium carbonate. The layers were separated and the aqueous layer extracted with 200 ml of methylene chloride. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered and evaporated to an oil. Addition of hexane gave the title product in crystalline form [11.3 g, m.p. 90°-98° C., Rf 0.5 (9:1 ethyl acetate:methanol)].

後処理

  1. temperaturethe mixture refluxed for 24 hours
  2. temperatureThe reaction mixture was cooled
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with 200 ml of methylene chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to an oil
  8. additionAddition of hexane

出典と根拠

ORDレコード
ord-4239bbcc50fb4d6496629e4c932b7af4
出典データセット
uspto-grants-1982_06
特許番号
US04337250

反応ノート

読み込み中…