Methyl iodide → HCID 86694710, compound

HRID 475157Notes

Reaction equation

HRID 475157 reaction equation
[F:1][C:2]1[C:16]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:15][C:5]2[N:6]([CH:9]3[CH2:14][CH2:13][CH2:12][CH2:11][O:10]3)[CH:7]=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].[CH3:28]I>C1COCC1>[F:1][C:2]1[C:16]([CH2:17][N:18]([CH3:28])[C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[CH:15][C:5]2[N:6]([CH:9]3[CH2:14][CH2:13][CH2:12][CH2:11][O:10]3)[CH:7]=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86694709HCID 86694709, compound

Product 1

HCID 86694710HCID 86694710, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

To a mixture of tert-butyl (5-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-6-yl)methylcarbamate (200 mg, 0.57 mmol) in anhydrous THF (2 mL) cooled to −60° C. was added NaH (60% in mineral oil, 21.6 mg, 0.9 mmol). After stirring at −60° C. for 30 min, CH3I (127 mg, 0.9 mmol) was added, followed by stirring at RT overnight. The reaction mixture was filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (3:1) to afford tert-butyl (5-fluoro-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-6-yl)methyl(methyl)carbamate as white solid (170 mg, 97%). MS (ESI): m/z=364 [M+1]+.

Workup

  1. stirringby stirring at RT overnight
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by SiO2 chromatography
  5. washeluting with petroleum ether/EtOAc (3:1)

Sources & evidence

ORD record
ord-092158d093ae47ee9a9cf3561b413d17
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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