Potassium Phosphate, Tribasic → 7-chloro-2-(4-cyclopropylpyridin-3-yl)-3,4-dihydroisoquinolin-1 (2H)-one

HRID 1844037Notes

Reaction equation

HRID 1844037 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.[CH:13]1([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2I)[CH2:15][CH2:14]1.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:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:16]=3[CH:13]3[CH2:15][CH2:14]3)[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 186723977-Chloro-3,4-dihydroisoquinolin-1(2H)-oneHCID 668018874-Cyclopropyl-3-iodopyridine

Product 1

HCID 569408217-chloro-2-(4-cyclopropylpyridin-3-yl)-3,4-dihydroisoquinolin-1 (2H)-oneYield 25.5%

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 4-cyclopropyl-3-iodopyridine (I-73c: 162 mg, 0.662 mmol), 1,4-dioxane (5 mL), copper iodide (31 mg, 0.165 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (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 (2% methanol in CHCl3) afforded 42 mg of the product (25.45% 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-ea8f7d00c6c94cd8b972d373e3518ca9
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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