Potassium Phosphate, Tribasic → HCID 66801648, compound

HRID 1843883Notes

Reaction equation

HRID 1843883 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][C:11]2=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].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>[CH3:22][C:21]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[N:10]1[CH:9]=[CH:8][C:7]2[C:12](=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:11]1=[O:14]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 131528427-Nitro-3,4-dihydroisoquinolin-1(2H)-oneHCID 144235133-Iodo-4-methylpyridine

Product 1

HCID 66801648HCID 66801648, compoundYield 23.9%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions as described in Example 1, 7-nitro-3,4-dihydro-2H-isoquinolin-1-one (I-24a: 400 mg, 2.0833 mmol) was reacted with 3-iodo-4-methyl-pyridine (456.2 mg, 2.08331 mmol), 1,4-dioxane (4.1 mL), copper iodide (39.6 mg, 0.2083 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (88.7 mg, 0.6249 mmol) and potassium phosphate (1.1 g, 5.2082 mmol) to afford the crude product. Purification by column chromatography on silica gel (50% ethylacetate in hexane) afforded 140 mg of the product (23.9% yield).

Workup

  1. customreaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (50% ethylacetate in hexane)

Sources & evidence

ORD record
ord-65d954fc473942faa3439c7856034701
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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