Potassium Phosphate, Tribasic → 6,7-Dimethoxy-2-(4-methyl-pyridin-3-yl)-3,4-dihydro-2H-isoquinolin-1-one

HRID 1843925Notes

Reaction equation

HRID 1843925 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[O:15])[NH:8][CH2:7][CH2:6]2.I[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[CH3:23].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[O:15])[N:8]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[CH3:23])[CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 610097CorydaldineHCID 144235133-Iodo-4-methylpyridine

Product 1

HCID 668073276,7-Dimethoxy-2-(4-methyl-pyridin-3-yl)-3,4-dihydro-2H-isoquinolin-1-oneYield 24.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions as described in Example 1, 6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one (I-40d: 100 mg, 0.483 mmol) was reacted with 3-iodo-4-methyl-pyridine (105 mg, 0.483 mmol), 1,4-dioxane (10 mL), copper iodide (9.2 mg, 0.0483 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (21.5 mg, 0.144 mmol) and potassium phosphate (255 mg, 1.207 mmol) to afford the crude product. Purification by column chromatography on silica gel (40% ethylacetate in hexane) afforded 35 mg of the product (24% yield).

Workup

  1. customreaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (40% ethylacetate in hexane)

Sources & evidence

ORD record
ord-f7a215a3479e44e0b30c1d555025d4e2
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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