1,10-Phenanthroline → HCID 44241777, compound

HRID 1775985Notes

Reaction equation

HRID 1775985 reaction equation
[CH3:1][CH:2]1[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][N:3]1[CH3:16])=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=3.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:40]#[C:41][C:42]1[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=1>C1(C)C=CC=CC=1>[Cl:48][C:45]1[CH:46]=[CH:47][C:42]([C:41]#[C:40][N:8]2[C:9]3[C:14](=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=3)[C:6]3[CH2:5][CH2:4][N:3]([CH3:16])[CH:2]([CH3:1])[C:7]2=3)=[CH:43][CH:44]=1

Participants

6

Reactant 4

HCID 13181,10-PhenanthrolineHCID 62657Potassium Phosphate, TribasicHCID 6403901-(Bromoethynyl)-4-chlorobenzeneHCID 66911784HCID 66911784, compound

Product 1

HCID 44241777HCID 44241777, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

1,2,6-trimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (214 mg, 1 mmol) 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)-1,2,6-trimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (67 mg) as brown semi solid. 1H NMR (CDCl3) FREE BASE 7.42 (d, 2H), 7.38 (d, 2H), 7.30 (m, 2H), 7.10 (d, 1H), 3.90 (m, 1H), 3.20 (m, 1H), 2.90 (m, 2H), 2.62 (m, 1H), 2.58 (s, 3H), 2.42 (s, 3H), 1.30 (d, 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-cddbaf077a144ed1a8639a06199fd983
Source dataset
uspto-grants-2016_02
Patent number
US09260429B2

Reaction notes

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