Methyl iodide → HCID 22277993, compound

HRID 1064085Notes

Reaction equation

HRID 1064085 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[N:12]([CH:20]([CH3:22])[CH3:21])[NH:11][C:10]2=[O:23])[CH:5]=[CH:6][C:7]=1[Cl:8].[Li+].[CH3:25][Si]([N-][Si](C)(C)C)(C)C.IC>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[N:12]([CH:20]([CH3:21])[CH3:22])[N:11]([CH3:25])[C:10]2=[O:23])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 22277996HCID 22277996, compound

Product 1

HCID 22277993HCID 22277993, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

In a 100 mL round bottom flask, was added 0.1 g 4-(3,4-Dichloro-phenyl)-1-isopropyl-5-pyridin-4-yl-pyrazolidin-3-one and 10 mL THF, stirred at 0° C. under nitrogen. 0.43 mL 1 M LHMDS in THF was added drop wise. After stirred at 0° C. for 30 min 0.026 mL iodomethane was added drop wise. The resulted mixture was stirred from 0° C. to rt for 2 hours, quenched with 20 mL sat. NH4Cl, extracted with dichloromethane 3×25 mL. The organic phase was dried over anhydrous Na2SO4. After purification by flash chromatography, obtained the title compound 80 mg as light solid. MS (ES+): 364 (M+H)+.

Workup

  1. additionwas added drop wise
  2. stirringThe resulted mixture was stirred from 0° C. to rt for 2 hours
  3. customquenched with 20 mL sat. NH4Cl
  4. extractionextracted with dichloromethane 3×25 mL
  5. dry with materialThe organic phase was dried over anhydrous Na2SO4
  6. customAfter purification by flash chromatography

Sources & evidence

ORD record
ord-ec2ae5d2c9194fb396efed0139f11d52
Source dataset
uspto-grants-2005_11
Patent number
US06967254B2

Reaction notes

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