Potassium Phosphate, Tribasic → HCID 66807323, compound

HRID 1844048Notes

Reaction equation

HRID 1844048 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.Br[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[C:20]([F:23])([F:22])[F:21].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[C:20]([F:23])([F:22])[F:21])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 107257096-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-oneHCID 199372633-Bromo-4-(trifluoromethyl)pyridine

Product 1

HCID 66807323HCID 66807323, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

6-Fluoro-3,4-dihydroisoquinolin-1(2H)-one (I-78d: 500 mg, 3.029 mmol) was reacted with 3-bromo-4-(trifluoromethyl)-pyridine (890 mg, 3.93 mmol), 1,4-dioxane (15 mL), copper iodide (57.5 mg, 0.30 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (43 mg, 0.302 mmol) and potassium phosphate (1.92 g, 9.08 mmol) for 36 hours at 120° C. to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3), afforded 600 mg of the product (64.5% 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-64fea84bcaa04b4380b5273164b73542
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

Loading…