Potassium Phosphate, Tribasic → HCID 56943053, compound

HRID 1843974Notes

Reaction equation

HRID 1843974 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][C:10]2=[O:13])=[CH:5][CH:4]=1.Br[C:17]1[N:21]([CH3:22])[CH:20]=[N:19][CH:18]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:22][N:21]1[C:17]([N:9]2[CH2:8][CH2:7][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

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 15152585-Bromo-1-methyl-1H-imidazoleHCID 668015937-(Trifluoromethyl)-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 56943053HCID 56943053, compoundYield 24.75%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous conditions as described for the preparation of Example 1A above, 7-(trifluoromethyl)-3,4-dihydroisoquinolin-1(2H)-one (I-4-d: 150 mg, 0.6849 mmol) was reacted with 5-bromo-1-methyl-1H-imidazole (165 mg, 1.0273 mmol), 1,4-dioxane (3 mL), copper iodide (13.01 mg, 0.0685 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (29.17 mg, 0.205 mmol) and potassium phosphate (434.6 mg, 2.05 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 50 mg of the product (24.75% yield).

Workup

  1. customas described for the preparation of Example 1A above
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (2% methanol in CHCl3)

Sources & evidence

ORD record
ord-ecbe8ac0d3af4f89a8aede058009f366
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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