Potassium Phosphate, Tribasic → HCID 56942729, compound

HRID 1843845Notes

Reaction equation

HRID 1843845 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH2:7][CH2:6]2.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:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[CH3:21])[CH2:7][CH2:6]2

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 106073926-methoxy-3,4-dihydroisoquinolin-1(2H)-oneHCID 144235133-Iodo-4-methylpyridine

Product 1

HCID 56942729HCID 56942729, compoundYield 53.1%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions as described in Example 1, 6-methoxy-3,4-dihydro-2H-isoquinolin-1-one (I-11d: 0.400 g, 2.2471 mmol) was reacted with 3-iodo-4-methyl-pyridine (0.492 g, 2.2471 mmol), 1,4-dioxane (40 mL), copper iodide (0.042 g, 0.2247 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (0.095 g, 0.6741 mmol) and potassium phosphate (1.190 g, 5.6177 mmol) to afford the crude product. Purification by column chromatography on silica gel (80% ethylacetate in hexane) afforded 0.320 g of the product (53% yield).

Workup

  1. customreaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (80% ethylacetate in hexane)

Sources & evidence

ORD record
ord-7b25cf0336cf4fcf943e8abf1a441601
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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