Potassium Phosphate, Tribasic → HCID 66807306, compound

HRID 1843874Notes

Reaction equation

HRID 1843874 reaction equation
[CH3:1][C:2]1([CH3:17])[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[C:5](=[O:16])[NH:4][CH2:3]1.Br[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1[CH3:25].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:1][C:2]1([CH3:17])[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:13])[F:14])=[CH:9][CH:10]=2)[C:5](=[O:16])[N:4]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][C:24]=2[CH3:25])[CH2:3]1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 8176303-Bromo-4-methylpyridineHCID 66807312HCID 66807312, compound

Product 1

HCID 66807306HCID 66807306, compoundYield 5.5%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions as described in Example 1, 4,4-dimethyl-7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one (I-20d: 200 mg, 0.8230 mmol) was reacted with 3-bromo-4-methyl-pyridine (91.9 mL, 0.8230 mmol), 1,4-dioxane (3 mL), copper iodide (15.6 mg, 0.0823 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (38.8 mL, 0.2469 mmol) and potassium phosphate (436.1 mg, 2.0575 mmol) to afford the crude product. Purification by column chromatography on silica gel (50% ethylacetate in hexane) afforded 15 mg of the product (5.44% yield).

Workup

  1. customreaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (50% ethylacetate in hexane)

Sources & evidence

ORD record
ord-500557f59aea4adda6212bcb536b2212
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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