Potassium Phosphate, Tribasic → HCID 56943051, compound

HRID 1843967Notes

Reaction equation

HRID 1843967 reaction equation
[F:1][C:2]([F:16])([F:15])[O:3][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.I[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[CH3:24].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:24][C:23]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[N:10]1[CH2:9][CH2:8][C:7]2[C:12](=[CH:13][C:4]([O:3][C:2]([F:1])([F:15])[F:16])=[CH:5][CH:6]=2)[C:11]1=[O:14]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 144235133-Iodo-4-methylpyridineHCID 64282065HCID 64282065, compound

Product 1

HCID 56943051HCID 56943051, compoundYield 5.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous conditions as described for the preparation of Example 1A above, 7-(trifluoromethoxy)-3,4-dihydroisoquinolin-1(2H)-one (I-51d: 160 mg, 0.6896 mmol) was reacted with 3-iodo-4-methyl-pyridine (151 mg, 0.6896 mmol), 1,4-dioxane (20 mL), copper iodide (13.1 mg, 0.0689 mmol), trans-N,N′-dimethyl-cyclohexyl-1, 2-diamine (29.3 mg, 0.2068 mmol) and potassium phosphate (365 mg, 1.724 mmol) to afford the crude product. Purification by column chromatography on silica gel (40% ethylacetate in hexane), followed by preparative HPLC afforded 12 mg of the product (5.4% yield).

Workup

  1. customas described for the preparation of Example 1A above
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (40% ethylacetate in hexane)

Sources & evidence

ORD record
ord-eb5bc6b3bd964f43ad601cdb3c70c25e
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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