Potassium Carbonate → 1-(5-Fluoro-pyridin-3-yl)-3-naphthalen-2-yl-imidazolidin-2-one

HRID 80106

Reaction equation

HRID 80106 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:15][CH2:14][NH:13][C:12]1=[O:16].Br[C:18]1[CH:19]=[N:20][CH:21]=[C:22]([F:24])[CH:23]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[F:24][C:22]1[CH:23]=[C:18]([N:13]2[CH2:14][CH2:15][N:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)[C:12]2=[O:16])[CH:19]=[N:20][CH:21]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 8202063-Bromo-5-fluoropyridineHCID 596361671-Naphthalen-2-yl-imidazolidin-2-one

Product 1

HCID 596361341-(5-Fluoro-pyridin-3-yl)-3-naphthalen-2-yl-imidazolidin-2-oneYield 57.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 79, 1-naphthalen-2-yl-imidazolidin-2-one (I-79b: 120 mg, 0.5681 mmol) was reacted with 3-bromo-5-fluoro-pyridine (100 mg, 0.5681 mmol), 1,4-dioxane (5 mL), copper iodide (10.82 mg, 0.05681 mmol), trans-1,2-diamino cyclohexane (19.51 mg, 0.1704 mmol) and potassium carbonate (157.07 mg, 1.1362 mmol) to afford the crude product. Purification by column chromatography on silica gel (30% EtOAc inhexane) afforded 100 mg of the product (57.15% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (30% EtOAc inhexane)

Sources & evidence

ORD record
ord-a65a9c6466c44d24ba8254fe1fa49654
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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