8-Hydroxyquinoline → HCID 66807415, compound

HRID 1843895Notes

Reaction equation

HRID 1843895 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.I[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[CH3:23].N1C2C(=CC=CC=2O)C=CC=1.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.CS(C)=O>[CH3:23][C:22]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N:9]1[CH:8]=[CH:7][C:6]2[C:11](=[CH:12][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:4][CH:5]=2)[C:10]1=[O:13]

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 144235133-Iodo-4-methylpyridineHCID 426091807-(Trifluoromethyl)isoquinolin-1(2H)-one

Product 1

HCID 66807415HCID 66807415, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Using analogous reaction conditions as described in Example 1, 7-trifluoromethyl-2H-isoquinolin-1-one (I-29d: 0.15 g, 0.0007 mol) was reacted with 3-iodo-4-methyl-pyridine (0.185 g, 0.8 mmol), DMSO (30 mL), copper iodide (0.026 g, 0.00014 mol), quinolin-8-ol (0.02 g, 0.14 mmol) and potassium carbonate (0.126 g, 0.9 mmol) to afford the crude product. Purification by column chromatography on silica gel (8% ethylacetate in hexane) afforded 0.055 g of the product (23.8% yield).

Workup

  1. customreaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (8% ethylacetate in hexane)

Sources & evidence

ORD record
ord-fda9fcfd9ca1422bacc98946bc1fcb90
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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