Potassium Phosphate, Tribasic → HCID 89964570, compound

HRID 1844028Notes

Reaction equation

HRID 1844028 reaction equation
[CH3:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:9]=2)[C:4](=[O:16])[NH:3]1.Br[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[C:24]([F:27])([F:26])[F:25].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([C:12]([F:13])([F:15])[F:14])=[CH:8][CH:9]=2)[C:4](=[O:16])[N:3]1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[C:24]([F:27])([F:26])[F:25]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 199372633-Bromo-4-(trifluoromethyl)pyridineHCID 66801674HCID 66801674, compound

Product 1

HCID 89964570HCID 89964570, compoundYield 3.9%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

3-Methyl-7-(trifluoromethyl)-3,4-dihydroisoquinolin-1(2H)-one (I-43d: 60 mg, 0.26 mmol) was reacted with 3-bromo-4-(trifluoromethyl)-pyridine (88 mg, 0.39 mmol), 1,4-dioxane (5 mL), copper iodide (14 mg, 0.078 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (3.7 mg, 0.026 mmol) and potassium phosphate (166 mg, 1.78 mmol) to afford the crude product. Purification by column chromatography on silica gel (1.5% methanol in CHCl3), followed by preparative HPLC afforded 3.8 mg of the product (3.8% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1.5% methanol in CHCl3)

Sources & evidence

ORD record
ord-03f79bfed62e42468d8b643201243d92
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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