Methyl iodide → HCID 9862178, compound

HRID 1007086Notes

Reaction equation

HRID 1007086 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([Br:17])=[CH:16][C:11]=2[NH:10][C:9]1=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].IC.[C:21]([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>CC#N>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([Br:17])=[CH:16][C:11]=2[N:10]([CH3:21])[C:9]1=[O:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 9796827HCID 9796827, compound

Product 1

HCID 9862178HCID 9862178, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-bromo-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester (4.0 g, 12.8 mmol), iodomethane (2.74 g, 9.2 mmol), and K2CO3 in CH3CN (60 mL) was stirred at room temperature under a blanket of nitrogen overnight. Upon completion of the reaction, ethyl acetate (200 mL) was added and the organic layer was washed with H2O (200 mL), dried over Na2SO4, and concentrated. The residue was purified via chromatography (silica gel, 25% ethyl acetate/hexane) to give 5-bromo-3-methyl-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester as a white solid: mp 98-99° C.; 1H-NMR (CDCl3) δ 7.7 (d, 1H, J=8.5 Hz), 7.27 (bs, 2H), 7.09 (d, 1H, J=2 Hz), 3.4 (s, 3H), 1.7 (s, 9H); MS (ES) m/z 349([M+Na]+, 20%), 351([M+Na]+, 20%); Anal. Calc. For C13H15BrN2O3: C, 47.73, H, 4.62, N, 8.56. Found: C, 47.46, H, 4.5, N, 8.29.

Workup

  1. additionwas added
  2. washthe organic layer was washed with H2O (200 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified via chromatography (silica gel, 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bcfd775e4c6b441d92cf2a0fff298e87
Source dataset
uspto-grants-2004_09
Patent number
US06794373B2

Reaction notes

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