Potassium Carbonate → 1-(1-Methyl-1H-indol-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80171Notes

Reaction equation

HRID 80171 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:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH3:24])[CH:19]=[CH:18]2.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:24][N:20]1[C:21]2[C:17](=[CH:16][C:15]([N:10]3[CH2:11][CH2:12][N:8]([C:3]4[CH:4]=[N:5][CH:6]=[CH:7][C:2]=4[CH3:1])[C:9]3=[O:13])=[CH:23][CH:22]=2)[CH:18]=[CH:19]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 2857575-Bromo-1-methyl-1H-indoleHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 596362651-(1-Methyl-1H-indol-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 27%

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: 150 mg, 0.847 mmol) was reacted with 5-bromo-1-methyl-1H-indole (215 mL, 1.016 mmol), 1,4-dioxane (20 mL), copper iodide (15 mg, 0.084 mmol), trans-1,2-diamino cyclohexane (0.03 mL, 0.254 mmol) and potassium carbonate (230 mg, 1.69 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3), followed by recrystallization using DCM and hexane afforded 55 mg of the product (27% yield).

Workup

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

Sources & evidence

ORD record
ord-9c45fc451cbc4020a9d2bfe58f517bc2
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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