Potassium Phosphate, Tribasic → HCID 56942728, compound

HRID 1843841Notes

Reaction equation

HRID 1843841 reaction equation
[C:1]1(=[O:15])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]3=2)[CH2:4][CH2:3][NH:2]1.I[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[CH3:23].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:23][C:22]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]3=[CH:7][CH:6]=2)[C:1]1=[O:15]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 12581538HCID 12581538, compoundHCID 144235133-Iodo-4-methylpyridine

Product 1

HCID 56942728HCID 56942728, compoundYield 55.47%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using analogous reaction conditions as described in Example 1, 3,4-dihydro-2H-benzo[h]isoquinolin-1-one (I-10d: 200 mg, 1.015 mmol) was reacted with 3-iodo-4-methyl-pyridine (266 mg, 1.214 mmol), 1,4-dioxane (15 mL), copper iodide (19 mg, 0.10 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (43 mg, 0.302 mmol) and potassium phosphate (538 mg, 2.53 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 162 mg of the product (55.47% yield).

Workup

  1. customreaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (1% methanol in CHCl3)

Sources & evidence

ORD record
ord-ce098b2490864d4484181334b0930b07
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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