Methyl iodide → HCID 86694704, compound

HRID 475138Notes

Reaction equation

HRID 475138 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2[N:9]=[CH:8][N:7]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][O:11]3)[C:6]=2[CH:16]=1.[H-].[Na+].[CH3:28]I>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:17][N:18]([CH3:28])[C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])[C:5]2[N:9]=[CH:8][N:7]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][O:11]3)[C:6]=2[CH:16]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86694703HCID 86694703, compound

Product 1

HCID 86694704HCID 86694704, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl (6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-4-yl)methylcarbamate (300 mg, 0.82 mmol) in DMF (10 mL) at 0° C. was added NaH (60% in mineral oil, 98.4 mg, 2.46 mmol). After stirring at RT for 30 min, CH3I (349 mg, 2.46 mmol) was added and the reaction mixture was stirred at RT overnight and then quenched with H2O at 0° C. The mixture was extracted with EtOAc (100 mL) and the extract washed with H2O (50 mL×3), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (1:1) to afford tert-butyl (6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-4-yl)methyl(methyl)carbamate as yellow oil (310 mg, 99%). MS (ESI): m/z=380.3 [M+1]+.

Workup

  1. stirringthe reaction mixture was stirred at RT overnight
  2. customquenched with H2O at 0° C
  3. extractionThe mixture was extracted with EtOAc (100 mL)
  4. washthe extract washed with H2O (50 mL×3)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by SiO2 chromatography
  9. washeluting with petroleum ether/EtOAc (1:1)

Sources & evidence

ORD record
ord-303577a4e11c4b8892e29c00886f79bc
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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