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

HRID 1388330Notes

Reaction equation

HRID 1388330 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-faf36233fe9b446ebdf723e23e674771
Source dataset
uspto-grants-1984_02
Patent number
US04431646

Reaction notes

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