Methanol → 1-(1H-indol-6-yl)-3-(4-methylpyridin-3-yl)imidazolidin-2-one

HRID 2383870Notes

Reaction equation

HRID 2383870 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[N:10]1[CH2:14][CH2:13][N:12]([C:15]2[CH:23]=[C:22]3[C:18]([CH:19]=[CH:20][N:21]3S(C3C=CC(C)=CC=3)(=O)=O)=[CH:17][CH:16]=2)[C:11]1=[O:34].CO>C(O)C.C(Cl)(Cl)Cl>[NH:21]1[C:22]2[C:18](=[CH:17][CH:16]=[C:15]([N:12]3[CH2:13][CH2:14][N:10]([C:5]4[CH:6]=[N:7][CH:8]=[CH:9][C:4]=4[CH3:3])[C:11]3=[O:34])[CH:23]=2)[CH:19]=[CH:20]1

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68788691HCID 68788691, compound

Product 1

HCID 596362581-(1H-indol-6-yl)-3-(4-methylpyridin-3-yl)imidazolidin-2-oneYield 47.54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
90 °C

Procedure

10% NaOH solution (10 mL) was added to a solution of 1-(4-methyl-pyridin-3-yl)-3-[1-(toluene-4-sulfonyl)-1H-indol-6-yl]-imidazolidin-2-one (I-144a: 94 mg) in ethanol (10 mL). The resulting mixture was heated to reflux at 90° C. for 1 hour. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was concentrated and partitioned between ethylacetate and water. The organic layer was washed with water, brine solution, dried and concentrated. Purification by column chromatography on silica gel (2% MeOH in DCM) afforded 29 mg of the product (47.54% yield).

Workup

  1. temperatureThe resulting mixture was heated
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethylacetate and water
  4. washThe organic layer was washed with water, brine solution
  5. customdried
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (2% MeOH in DCM)

Sources & evidence

ORD record
ord-f501c8428cb44490a9c90aa8bc2e6170
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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