8-Hydroxyquinoline → HCID 89964859, compound

HRID 1844020Notes

Reaction equation

HRID 1844020 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][NH:9][C:10]2=[O:13])=[CH:5][CH:4]=1.Br[C:17]1[CH:18]=[N:19][CH:20]=[C:21]([F:23])[CH:22]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.[Cu]I.O1CCOCC1>[F:23][C:21]1[CH:22]=[C:17]([N:9]2[CH:8]=[CH:7][C:6]3[C:11](=[CH:12][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:4][CH:5]=3)[C:10]2=[O:13])[CH:18]=[N:19][CH:20]=1

Participants

8

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 8202063-Bromo-5-fluoropyridineHCID 426091807-(Trifluoromethyl)isoquinolin-1(2H)-one

Product 1

HCID 89964859HCID 89964859, compoundYield 47.14%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

7-Trifluoromethyl-2H-isoquinolin-1-one (I-29d: 0.1 g, 0.00046 mol) was reacted with 3-bromo-5-fluoropyridine (0.099 g, 0.00056 mol), 8-hydroxy quinoline (0.013 g, 0.00009 mol), K2CO3 (0.161 g, 0.0011 mol), CuI (0.017 g, 0.00009 mol) and 1,4-dioxane (5 mL) to afford the crude product. The reaction mass was cooled to room temperature, diluted with DCM, washed with ammonia solution and separated the layers. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (0.5% methanol in DCM), followed by hexane-wash afforded 66.5 mg of the product (47.14% yield).

Workup

  1. customto afford the crude product
  2. washwashed with ammonia solution
  3. customseparated the layers
  4. washThe organic layer was washed with brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford the crude product
  8. customPurification by column chromatography on silica gel (0.5% methanol in DCM)
  9. washwash

Sources & evidence

ORD record
ord-99e5fd5ab29342e48c86c20663508b12
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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