Potassium Phosphate, Tribasic → HCID 56942732, compound

HRID 1843868Notes

Reaction equation

HRID 1843868 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH2:7][CH2:6]2.I[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[CH3:23].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:23][C:22]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:2]([F:1])([F:14])[F:15])[CH:4]=2)[C:9]1=[O:13]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 144235133-Iodo-4-methylpyridineHCID 668017026-(Trifluoromethyl)-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 56942732HCID 56942732, compoundYield 9.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions as described in Example 1, 6-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one (I-17c: 150 mg, 0.698 mmol) was reacted with 3-iodo-4-methyl-pyridine (152.8 mg, 0.698 mmol), 1,4-dioxane (10 mL), copper iodide (13.3 mg, 0.0698 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (29.73 mg, 0.209 mmol) and potassium phosphate (369.94 mg, 1.745 mmol) to afford the crude product. Purification by column chromatography on silica gel (1.5% methanol in DCM) afforded 20 mg of the product (9.38% yield).

Workup

  1. customreaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (1.5% methanol in DCM)

Sources & evidence

ORD record
ord-a064171501ab4186a82816bdd5614bba
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

Loading…