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

HRID 2296026Notes

Reaction equation

HRID 2296026 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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)].

Workup

  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

Sources & evidence

ORD record
ord-645a346f2f0849e08fbb184fd40e82b8
Source dataset
uspto-grants-1984_01
Patent number
US04427679

Reaction notes

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