1,10-Phenanthroline → 9-((4-chlorophenyl)ethynyl)-1-ethyl-2,6-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

HRID 2198374Notes

Reaction equation

HRID 2198374 reaction equation
[CH3:1][N:2]1[CH2:14][CH2:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH3:15])[CH:10]=3)[NH:5][C:4]=2[CH:3]1[C:16]1C=CC=C[CH:17]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:45]#[C:46][C:47]1[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49][CH:48]=1>C1(C)C=CC=CC=1>[Cl:53][C:50]1[CH:51]=[CH:52][C:47]([C:46]#[C:45][N:5]2[C:6]3[C:11](=[CH:10][C:9]([CH3:15])=[CH:8][CH:7]=3)[C:12]3[CH2:13][CH2:14][N:2]([CH3:1])[CH:3]([CH2:16][CH3:17])[C:4]2=3)=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 13181,10-PhenanthrolineHCID 62657Potassium Phosphate, TribasicHCID 6403901-(Bromoethynyl)-4-chlorobenzeneHCID 66911787HCID 66911787, compound

Product 1

HCID 579304799-((4-chlorophenyl)ethynyl)-1-ethyl-2,6-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

2,6-dimethyl-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (276 mg, μmol) was mixed with CuSO4.5H2O (50 mg, 0.2 mmol), 1,10-phenanthroline (72 mg, 0.4 mmol), K3PO4 (425 mg, 2 mmol) and 1-(bromoethynyl)-4-chlorobenzene (237 mg, 1.1 mmol) in toluene (8-10 ml). The reaction mixture was flushed with nitrogen and heated at 80° C. for 16 h. The reaction mixture was filtered through Celite, and the Celite bed was rinsed with dichloromethane. Combined organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography (100-200 mesh) eluting with 60-80% ethyl acetate in hexane to obtain 9-((4-chlorophenyl)ethynyl)-1-ethyl-2,6-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole as brown semi solid (90 mg). 1H NMR (CDCl3) FREE BASE7.40-7.20 (m, 9H), 7.16-7.12 (d, 1H), 7.08-7.04 (d, 2H), 4.73 (s, 1H), 3.22-3.16 (m, 1H), 3.0-2.80 (m, 3H), 2.50 (s, 3H), 2.45 (s, 3H).

Workup

  1. customThe reaction mixture was flushed with nitrogen
  2. filtrationThe reaction mixture was filtered through Celite
  3. washthe Celite bed was rinsed with dichloromethane
  4. concentrationCombined organic layer was concentrated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (100-200 mesh)
  6. washeluting with 60-80% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3005f3b43b804e10a8ac62b5eee9d2b9
Source dataset
uspto-grants-2012_12
Patent number
US08338447B2

Reaction notes

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