Potassium Phosphate, Tribasic → HCID 89964092, compound

HRID 1844024Notes

Reaction equation

HRID 1844024 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2.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>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH3:20])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 144235133-Iodo-4-methylpyridineHCID 228908916-Methyl-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 89964092HCID 89964092, compoundYield 31.9%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

6-Methyl-3,4-dihydroisoquinolin-1(2H)-one (I-69f: 2 g, 12.422 mmol) was reacted with 3-iodo-4-methyl-pyridine (2.72 g, 12.422 mmol), 1,4-dioxane (70 mL), copper iodide (236 mg, 1.2422 mmol), trans-N,N′-dimethyl-cyclohexyl-1, 2-diamine (530 mg, 3.727 mmol) and potassium phosphate (6.58 g, 31.055 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% methanol in DCM) afforded 1 g of the product (31.8% yield).

Workup

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

Sources & evidence

ORD record
ord-0247a79efc2f47e98bb79edc95c0b645
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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