1,10-Phenanthroline → HCID 59455109, compound

HRID 1400614Notes

Reaction equation

HRID 1400614 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.Br[C:37]#[C:38][Si:39]([CH:46]([CH3:48])[CH3:47])([CH:43]([CH3:45])[CH3:44])[CH:40]([CH3:42])[CH3:41]>C1(C)C=CC=CC=1.O.S([O-])([O-])(=O)=O.[Cu+2]>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:37]#[C:38][Si:39]([CH:40]([CH3:42])[CH3:41])([CH:46]([CH3:48])[CH3:47])[CH:43]([CH3:45])[CH3:44])[C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 196158-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indoleHCID 11196280(2-Bromoethynyl)tris(propan-2-yl)silane

Product 1

HCID 59455109HCID 59455109, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a stirred solution of 8-chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (10 g, 0.0454 mol) and copper sulfate (1.13 g, 0.00454 mol) in toluene (100 mL) was added potassium carbonate (12.5 g, 0.0909 mol) and 1,10 phenanthroline (1.6 g, 0.00909 mol). The reaction mixture was stirred for 5 min at RT. Bromoethynyl triisopropylsilane (13.0 g, 0.0499 mol) was added to the reaction mixture at the same temperature. After completion of addition, the reaction mixture was stirred overnight at 80° C. After completion of reaction (monitored by TLC), the mixture was cooled to RT, diluted with water (500 mL), and extracted with EtOAc (3×500 mL). The organic layer was dried over anhydrous sodium sulfate and solvent was removed under pressure. The product was purified by column chromatography (1% MeOH:DCM in silica 100-200 mesh, diameter of column—5 cm, height of silica—approx. 5 inch) to provide the desired compound as a dark brown colored oil (8.0 g, 44% yield).

Workup

  1. additionAfter completion of addition
  2. stirringthe reaction mixture was stirred overnight at 80° C
  3. customAfter completion of reaction (monitored by TLC)
  4. temperaturethe mixture was cooled to RT
  5. extractionextracted with EtOAc (3×500 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate and solvent
  7. customwas removed under pressure
  8. customThe product was purified by column chromatography (1% MeOH:DCM in silica 100-200 mesh, diameter of column—5 cm, height of silica—approx. 5 inch)

Sources & evidence

ORD record
ord-3be2b2bf3c6143babbe6b29ea45cf25d
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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