Potassium Phosphate, Tribasic → HCID 66807344, compound

HRID 1843824Notes

Reaction equation

HRID 1843824 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][NH:14][C:15]3=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.I[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][C:25]=1[CH3:26].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][N:14]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][C:25]=4[CH3:26])[C:15]3=[O:18])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 144235133-Iodo-4-methylpyridineHCID 66803463HCID 66803463, compound

Product 1

HCID 66807344HCID 66807344, compoundYield 11.1%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions as described in example 1, 7-(4-fluoro-phenyl)-3,4-dihydro-2H-isoquinolin-1-one (100 mg, 0.4132 mmol) was reacted with 3-iodo-4-methyl-pyridine (108.5 mg, 0.4958 mmol), 1,4-dioxane (25 mL), copper iodide (2.8 mg, 0.01432 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (14.2 mg, 0.1239 mmol) and potassium phosphate (219.2 mg, 1.0330 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3), followed by preparative HPLC afforded 15 mg of the product (11.1% yield).

Workup

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

Sources & evidence

ORD record
ord-241994ae596b42b5afe27de18075544b
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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