Potassium Phosphate, Tribasic → HCID 56942727, compound

HRID 1843821Notes

Reaction equation

HRID 1843821 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.I[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH3:20].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:19]=3[CH3:20])[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 144235133-Iodo-4-methylpyridineHCID 186723977-Chloro-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 56942727HCID 56942727, compoundYield 31.25%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions as described in Example 1, 7-chloro-3,4-dihydro-2H-isoquinolin-1-one (I-1d: 150 mg, 0.824 mmol) was reacted with 3-iodo-4-methyl-pyridine (216 mg, 0.989 mmol), 1,4-dioxane (10 mL), copper iodide (15.69 mg, 0.0824 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (35.10 mg, 0.2472 mmol) and potassium phosphate (524 mg, 2.472 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 70 mg of the product (31.25% yield).

Workup

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

Sources & evidence

ORD record
ord-c8bd74f77145484b8edf57f93507b5c8
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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