Potassium Phosphate, Tribasic → HCID 66802002, compound

HRID 1844056Notes

Reaction equation

HRID 1844056 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2.I[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH3:20].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH3:20])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 107257096-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-oneHCID 144235133-Iodo-4-methylpyridine

Product 1

HCID 66802002HCID 66802002, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

6-Fluoro-3,4-dihydroisoquinolin-1(2H)-one (I-78d: 250 mg, 1.5146 mmol) was reacted with 3-iodo-4-methyl-pyridine (365 mg, 1.66 mmol), 1,4-dioxane (10 mL), copper iodide (29 mg, 0.151 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (21.5 mg, 0.151 mmol) and potassium phosphate (965 mg, 4.54 mmol) for 14 hours at 120° C. to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 350 mg of the product (90.4% yield).

Workup

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

Sources & evidence

ORD record
ord-7bec6adddcdf484fa048581b4e47d581
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

Loading…