Potassium Phosphate, Tribasic → HCID 56942893, compound

HRID 1843906Notes

Reaction equation

HRID 1843906 reaction equation
[Cl:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][C:9]2=[O:13])=[CH:4][CH:3]=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>[Cl:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][C:20]=3[CH3:21])[C:9]2=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 144235133-Iodo-4-methylpyridineHCID 66801876HCID 66801876, compound

Product 1

HCID 56942893HCID 56942893, compoundYield 28.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions as described in Example 1, 7-chloro-8-fluoro-3,4-dihydro-2H-isoquinolin-1-one (I-33d: 150 mg, 0.753 mmol) was reacted with 3-iodo-4-methyl-pyridine (165 mg, 0.73 mmol), 1,4-dioxane (10 mL), copper iodide (143 mg, 0.075 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (32 mg, 0.225 mmol) and potassium phosphate (399 mg, 1.88 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 60 mg of the product (27.6% 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-1dc90a52ee5f4c57811cbabfa830ca11
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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