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Sodium hydride → 3-(1-acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione

HRID 546561
Notes
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Reaction equation

HRID 546561 reaction equation
[H-].[Na+].[C:3]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N:15]3[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[NH:17][C:16]3=[O:23])[CH:13]=2)[C:8]([CH3:25])([CH3:24])[CH2:7]1)(=[O:5])[CH3:4].[Cl:26][C:27]1[CH:32]=[C:31]([CH2:33]Cl)[CH:30]=[CH:29][N:28]=1>CN(C)C=O.O>[C:3]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N:15]3[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[N:17]([CH2:33][C:31]4[CH:30]=[CH:29][N:28]=[C:27]([Cl:26])[CH:32]=4)[C:16]3=[O:23])[CH:13]=2)[C:8]([CH3:25])([CH3:24])[CH2:7]1)(=[O:5])[CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 111265732-Chloro-4-(chloromethyl)pyridineHCID 576259993-(1-Acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-5,5-dimethyl-imidazolidine-2,4-dione

Product 1

HCID 576259663-(1-acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dioneYield 92.6%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
25 °C

Procedure

To 949 mg of sodium hydride are added dropwise, under argon, 5 mL of dimethylformamide, followed by addition of a solution of 6.8 g of 3-(1-acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-5,5-dimethylimidazolidine-2,4-dione obtained in stage g) below in 40 mL of dimethylformamide. The solution obtained is stirred for 1.5 hours at 25° C., followed by addition of 5.24 g of 2-chloro-4-chloromethylpyridine obtained in stage b) below. The reaction mixture is stirred at room temperature for 15 hours and diluted with 300 mL of water, and the solid formed is filtered off, washed with three times 20 mL of water and with twice 20 mL of diethyl ether and dried to give 8.8 g of 3-(1-acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-1-[(2-chloropyridin-4-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione in the form of a beige-coloured solid, the characteristics of which are as follows:

Workup

  1. customThe solution obtained
  2. stirringThe reaction mixture is stirred at room temperature for 15 hours
  3. customthe solid formed
  4. filtrationis filtered off
  5. washwashed with three times 20 mL of water and with twice 20 mL of diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-f78c8d64115c419ab40bdfdf6b27dc0b
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935819B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes