Selenium Dioxide → HCID 178445806, compound

HRID 713941Notes

Reaction equation

HRID 713941 reaction equation
[Se](=O)=[O:2].[Br:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH:16]3[CH2:21][CH2:20][CH:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:18][CH2:17]3)[CH:13]=2)[N:8]=[C:7]([CH3:26])[CH:6]=1>O1CCOCC1>[Br:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C@H:16]3[CH2:21][CH2:20][C@H:19]([C:22]([CH3:23])([CH3:25])[CH3:24])[CH2:18][CH2:17]3)[CH:13]=2)[N:8]=[C:7]([CH:26]=[O:2])[CH:6]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 669265584-Bromo-6-(4-tert-butyl-cyclohexyloxy)-2-methyl-quinoline

Product 1

HCID 178445806HCID 178445806, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a suspension of Selenium dioxide (0.333 g, 3.00 mmol) in 1,4-Dioxane (8.0 mL) was added a solution of 4-Bromo-6-(4-tert-butyl-cyclohexyloxy)-2-methyl-quinoline (0.469 g, 1.25 mmol) in 1,4-Dioxane (4.0 mL). The mixture was sealed and was heated at 50° C. in an oil bath. After 4 d, the reaction was filtered through Celite and washed with dioxane. The solvent was evaporated and the residue was purified on silica gel column using 0-25% ethyl acetate in hexanes as eluent. Isolated was the product (Rf=0.68 in 3:1 hexanes/ethyl acetate) in 362 mg yield, 74%. ESI (M+H+): 390.10/392.10.

Workup

  1. customThe mixture was sealed
  2. filtrationthe reaction was filtered through Celite
  3. washwashed with dioxane
  4. customThe solvent was evaporated
  5. customthe residue was purified on silica gel column
  6. customIsolated
  7. customyield

Sources & evidence

ORD record
ord-041590d9aa80437b90d29a5773cdd832
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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