Potassium Phosphate, Tribasic → HCID 56940826, compound

HRID 1844063Notes

Reaction equation

HRID 1844063 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[C:8](=[O:16])[NH:7][CH2:6][CH2:5]2.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>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([F:14])([F:13])[F:15])[C:8](=[O:16])[N:7]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[C:24]([F:27])([F:26])[F:25])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 199372633-Bromo-4-(trifluoromethyl)pyridineHCID 66801981HCID 66801981, compound

Product 1

HCID 56940826HCID 56940826, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

6-Chloro-7-(trifluoromethyl)-3,4-dihydroisoquinolin-1(2H)-one (I-85e: 100 mg, 0.4 mmol) was reacted with 3-bromo-4-(trifluoromethyl)-pyridine (117.6 mg, 0.520 mmol), 1,4-dioxane (5 mL), copper iodide (7.6 mg, 0.04 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (5.6 mg, 0.04 mmol) and potassium phosphate (255.6 mg, 1.2 mmol) to afford the crude product. Purification by preparative HPLC afforded 15 mg of the product (10% yield).

Workup

  1. customto afford the crude product
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-7a64812a3f9e4566b87d1dfc2e5bd3b3
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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