Methyl iodide → HCID 58542022, compound

HRID 1966756Notes

Reaction equation

HRID 1966756 reaction equation
[Br:1][C:2]1[CH:26]=[CH:25][C:5]2[N:6]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]3[O:19][C:18](=[O:20])[NH:17][N:16]=3)=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].[CH3:29]I>CN(C=O)C>[Br:1][C:2]1[CH:26]=[CH:25][C:5]2[N:6]([C:21]([CH3:23])([CH3:22])[CH3:24])[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]3[O:19][C:18](=[O:20])[N:17]([CH3:29])[N:16]=3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58541943HCID 58541943, compound

Product 1

HCID 58542022HCID 58542022, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a round bottom flask is added 5-[2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-phenyl]-3H-[1,3,4]oxadiazol-2-one (100 mg, 0.242 mmol) in DMF (4 mL) at 0° C., followed by the addition of NaH (19 mg, 0.475 mmol). The reaction mixture is stirred at 0° C. for 10 minutes, followed by the addition of MeI (103 mg, 0.726 mmol). The reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is quenched with saturated NH4Cl (10 mL) and extracted with EtOAc (20 mL). The organic layer is separated, washed with brine, dried under anhydrous Na2SO4, filtered and concentrated. The residue is purified by silica gel flash chromatography with 0-5% MeOH/CH2Cl2 as the eluent to afford 5-[2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-phenyl]-3-methyl-3H-[1,3,4]oxadiazol-2-one (92 mg, 89%) as a solid. LCMS (ESMS): m/z 427.63, 429.67 (M++1).

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 2 hours
  2. customThe reaction mixture is quenched with saturated NH4Cl (10 mL)
  3. extractionextracted with EtOAc (20 mL)
  4. customThe organic layer is separated
  5. washwashed with brine
  6. customdried under anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified by silica gel flash chromatography with 0-5% MeOH/CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-b8056fece2d04bd1a0bbf1c69c7f0c62
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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