Potassium Phosphate, Tribasic → HCID 56940827, compound

HRID 1844067Notes

Reaction equation

HRID 1844067 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][C:9]2=[O:12])=[CH:4][C:3]=1[O:13][CH3:14].I[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:21]=1[CH3:22].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:21]=3[CH3:22])[C:9]2=[O:12])=[CH:4][C:3]=1[O:13][CH3:14]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 144235133-Iodo-4-methylpyridineHCID 66801970HCID 66801970, compound

Product 1

HCID 56940827HCID 56940827, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

7-Chloro-6-methoxy-3,4-dihydroisoquinolin-1(2H)-one (I-86d: 200 mg, 0.946 mmol) was reacted with 3-iodo-4-methylpyridine (228.2 mg, 1.042 mmol), 1,4-dioxane (5 mL), copper iodide (18 mg, 0.094 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (13.4 mg, 0.095 mmol) and potassium phosphate (603.3 mg, 2.84 mmol) for 48 hours at 120° C. to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 150 mg of the product (52.4% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% methanol in CHCl3)

Sources & evidence

ORD record
ord-05ef9eb05f1244bb9a4a6401f34759db
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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