1,10-Phenanthroline → HCID 59454929, compound

HRID 1401680Notes

Reaction equation

HRID 1401680 reaction equation
[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]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]>[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[N:6]([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:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

8

Reactant 4

HCID 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-HCID 11196280(2-Bromoethynyl)tris(propan-2-yl)silane

Product 1

HCID 59454929HCID 59454929, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a stirred solution of 2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (10 g, 0.05 mol) and copper sulfate (1.24 g, 0.005 mol) in toluene (200 mL) was added potassium carbonate (13.8 g, 0.1 mol) and 1,10 phenanthroline (1.8 g, 0.01 mol). The reaction mixture was stirred for 5 min at RT. (Bromoethynyl)triisopropylsilane (14.4 g, 0.055 mol) was added to the reaction mixture at the same temperature. After completion of addition, the reaction mixture was stirred overnight at 80° C. The reaction was monitored by TLC. After completion of reaction, 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 reduced pressure. The crude 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 (9.5 g, 50% yield).

Workup

  1. additionAfter completion of addition
  2. stirringthe reaction mixture was stirred overnight at 80° C
  3. customAfter completion of reaction
  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 reduced pressure
  8. customThe crude 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-9daf7b199fb34e22b131e5a18bcff574
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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