Potassium Phosphate, Tribasic → HCID 66802170, compound

HRID 1843940Notes

Reaction equation

HRID 1843940 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:14].[O-]P([O-])([O-])=O.[K+].[K+].[K+].I[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][C:29]=1[CH3:30].CN[C@@H]1CCCC[C@H]1NC>O1CCOCC1.CCCCCC.[Cu]I.C(OC(=O)C)C>[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][C:29]=1[CH3:30])[C:7]2=[O:14]

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 144235133-Iodo-4-methylpyridineHCID 66801841HCID 66801841, compound

Product 1

HCID 66802170HCID 66802170, compoundYield 14.75%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

5-Fluoro-8-methoxy-3,4-dihydro-2H-isoquinolin-1-one (I-44d: 0.12 g, 0.6 mmol) was refluxed with K3PO4 (0.32 g, 1.5 mmol), 3-Iodo-4-methyl-pyridine (0.175 g, 0.79 mmol), trans-N,N′-dimethyl-cyclohexane-1,2-diamine (0.026 g, 0.18 mmol) and CuI (0.01 g, 0.06 mmol) in 1,4-dioxane (20 mL) at 120° C. overnight. The reaction was monitored by TLC (80% ethylacetate in hexane). The reaction mass was cooled to room temperature, filtered and partitioned between DCM and water. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated. Purification by column chromatography on silica gel (2% methanol in chloroform) followed by preparative HPLC afforded 25 mg of the product (14.75% yield).

Workup

  1. filtrationfiltered
  2. custompartitioned between DCM and water
  3. washThe organic layer was washed with water, brine solution
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel (2% methanol in chloroform)

Sources & evidence

ORD record
ord-b095e8b252e9457ea1b0ff7ade517813
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

Loading…