Methyl iodide → HCID 22277998, compound

HRID 1064090Notes

Reaction equation

HRID 1064090 reaction equation
[CH:1]1([CH2:7][N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH:11]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=3)[C:10](=[O:27])[NH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[CH3:29][Si]([N-][Si](C)(C)C)(C)C.IC>C1COCC1>[CH:1]1([CH2:7][N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH:11]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=3)[C:10](=[O:27])[N:9]2[CH3:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 22278001HCID 22278001, compound

Product 1

HCID 22277998HCID 22277998, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

In a 100 mL round bottom flask, was added 0.4 g 1-Cyclohexylmethyl-4-(3,4-dichloro-phenyl)-5-pyridin-4-yl-pyrazolidin-3-one and 20 mL THF, stirred at 0° C. under nitrogen. 1.32 mL 1 M LHMDS in THF was added drop wise. After stirred at 0° C. for 30 min. 0.11 mL iodomethane was added drop wise. The resulted mixture was stirred from 0° C. to rt for 2 hour, quenched with 50 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 0.4 g as light solid. MS (ES+): 418 (M+H)+.

Workup

  1. stirringAfter stirred at 0° C. for 30 min
  2. stirringThe resulted mixture was stirred from 0° C. to rt for 2 hour
  3. customquenched with 50 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-010f13a294ec41b9969f3b6adeab9adb
Source dataset
uspto-grants-2005_11
Patent number
US06967254B2

Reaction notes

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