Potassium Phosphate, Tribasic → HCID 56940822, compound

HRID 1844038Notes

Reaction equation

HRID 1844038 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.Br[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH2:20][CH3:21].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:19]=3[CH2:20][CH3:21])[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 131605333-Bromo-4-ethylpyridineHCID 186723977-Chloro-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 56940822HCID 56940822, compoundYield 15.8%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

7-Chloro-3,4-dihydroisoquinolin-1(2H)-one (I-1d: 100 mg, 0.552 mmol) was reacted with 3-bromo-4-ethyl pyridine (133.5 mg, 0.718 mmol), 1,4-dioxane (5 mL), copper iodide (10.48 mg, 0.0555 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (7.8 mg, 0.055 mmol) and potassium phosphate (351 mg, 1.657 mmol for 48 hours at 120° C. to afford the crude product. Purification by column chromatography on silica gel (50% ethyl acetate in hexane), followed by preparative HPLC afforded 25 mg of the product (15.72% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-a12a2fa902b94b3ca98dbf5647067d9a
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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