Potassium Phosphate, Tribasic → HCID 56942891, compound

HRID 1843889Notes

Reaction equation

HRID 1843889 reaction equation
[CH3:1][O:2][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.I[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[CH3:21].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][C:20]=3[CH3:21])[C:10]2=[O:13])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 135216727-Methoxy-3,4-dihydroisoquinolin-1(2H)-oneHCID 144235133-Iodo-4-methylpyridine

Product 1

HCID 56942891HCID 56942891, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions as described in Example 1, 7-methoxy-3,4-dihydro-2H-isoquinolin-1-one (I-26b: 400 mg, 2.259 mmol) was reacted with 3-iodo-4-methyl-pyridine (495 mg, 2.259 mmol), 1,4-dioxane (25 mL), copper iodide (43 mg, 0.225 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (96.23 mg, 0.677 mmol) and potassium phosphate (1.197 g, 5.647 mmol) to afford the crude product. Purification by column chromatography on silica gel (40% ethylacetate in hexane) afforded 170 mg of the product (23% 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-776a883c8e9d46a3aa43d97d4d918c81
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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