Potassium Phosphate, Tribasic → HCID 66802250, compound

HRID 1844053Notes

Reaction equation

HRID 1844053 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.I[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH:20]1[CH2:22][CH2:21]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH:20]1([C:19]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[N:7]2[CH2:6][CH2:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=3)[C:8]2=[O:12])[CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 107257096-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-oneHCID 668018874-Cyclopropyl-3-iodopyridine

Product 1

HCID 66802250HCID 66802250, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

6-Fluoro-3,4-dihydroisoquinolin-1(2H)-one (I-78d: 500 mg, 3.02938 mmol) was reacted with 3-iodo-4-cyclopropyl-pyridine 816 mg, 3.3323 mmol), 1,4-dioxane (10 mL), copper iodide (57.3 mg, 0.3 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (43 mg, 0.30 mmol) and potassium phosphate (1.92 g, 9.0 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 700 mg of the product (81.9% 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-3ca00eb73a7a4de1ac431ed4da8907f0
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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