Potassium Phosphate, Tribasic → HCID 56940969, compound

HRID 1844071Notes

Reaction equation

HRID 1844071 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].[CH:15]1([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2I)[CH2:17][CH2:16]1.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:19]3[CH:20]=[N:21][CH:22]=[CH:23][C:18]=3[CH:15]3[CH2:17][CH2:16]3)[C:9]2=[O:12])=[CH:4][C:3]=1[O:13][CH3:14]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 668018874-Cyclopropyl-3-iodopyridineHCID 66801970HCID 66801970, compound

Product 1

HCID 56940969HCID 56940969, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

7-Chloro-6-methoxy-3,4-dihydroisoquinolin-1(2H)-one 100 mg, 0.473 mmol) was reacted with 4-cyclopropyl-3-iodopyridine (I-73c: 127.6 mg, 0.521 mmol), 1,4-dioxane (5 mL), copper iodide (9.3 mg, 0.047 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (6.7 mg, 0.047 mmol) and potassium phosphate (301.6 mg, 1.421 mmol) for 12 hours at 120° C. to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3), followed by preparative HPLC afford 35 mg of the product

Workup

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

Sources & evidence

ORD record
ord-691a97c9fb4049b793d2f5b3e40c5a43
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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