1,2-Diaminocyclohexane, trans- → 2-Fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde

HRID 80153

Reaction equation

HRID 80153 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13].Br[C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[C:17]([F:23])[CH:16]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[F:23][C:17]1[CH:16]=[C:15]([N:10]2[CH2:11][CH2:12][N:8]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:2]=3[CH3:1])[C:9]2=[O:13])[CH:22]=[CH:21][C:18]=1[CH:19]=[O:20]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 596361642-Fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehydeYield 59.2%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 300 mg, 1.694 mmol) was reacted with 4-bromo-2-fluoro-benzaldehyde (403 mg, 2.118 mmol), 1,4-dioxane (25 mL), copper iodide (32.186 mg, 0.1694 mmol), trans-1,2-diamino cyclohexane (72.16 mg, 0.5082 mmol) and potassium phosphate (1.077 g, 5.082 mmol) to afford the crude product. Purification by column chromatography on silica gel (1.5% MeOH in CHCl3) afforded 300 mg of 2-Fluoro-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde (59.05% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1.5% MeOH in CHCl3)

Sources & evidence

ORD record
ord-1b2fa23761714a5ca6494edf7fb5ff0a
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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