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

HRID 1388351노트

반응식

HRID 1388351 반응식
[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

참가 물질

7

반응물 5

HCID 4875Potassium IodideHCID 10340Sodium Carbonate2회HCID 112513-Methyl-2-butanoneHCID 810936-BromohexanenitrileHCID 126299068-fluoro-5-(4-fluorophenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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)].

후처리

  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

출처 및 근거

ORD 기록
ord-da8077c360ae439fa071722e0045100b
출처 데이터셋
uspto-grants-1984_02
특허 번호
US04431649

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