Potassium Phosphate, Tribasic → HCID 56943054, compound

HRID 1843978Notes

Reaction equation

HRID 1843978 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[C:8](=[O:13])[NH:7][CH2:6][CH2:5]2.Br[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[C:21]([F:24])([F:23])[F:22].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[C:8](=[O:13])[N:7]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[C:21]([F:24])([F:23])[F:22])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 141771016,7-Dichloro-3,4-dihydro-2H-isoquinolin-1-oneHCID 199372633-Bromo-4-(trifluoromethyl)pyridine

Product 1

HCID 56943054HCID 56943054, compoundYield 8.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using an analogous procedure and workup as described for the preparation of Example 1A above, 6,7-dichloro-3,4-dihydroisoquinolin-1(2H)-one (I-55d: 100 mg, 0.463 mmol) was reacted with 3-bromo-4-(trifluoromethyl)pyridine (115 mg, 0.509 mmol), 1,4-dioxane (3 mL), copper iodide (7 mg, 0.046 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (20 mg, 0.1388 mmol) and potassium phosphate (245 mg, 1.157 mmol) in a sealed tube at 120° C. for 16 hours to afford the crude product. Purification by column chromatography on silica gel (20% ethylacetate in hexane) afforded 14 mg of the product (8.3% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (20% ethylacetate in hexane)

Sources & evidence

ORD record
ord-0b202715be644a648d4a135f342adfd8
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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