Methyl iodide → HCID 58542030, compound

HRID 1966749Notes

Reaction equation

HRID 1966749 reaction equation
[Br:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]3[N:19]=[CH:18][NH:17][N:16]=3)=[N:8][C:4]=2[CH:3]=1.[C:26]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]([C:20]([CH3:22])([CH3:21])[CH3:23])[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]3[N:19]=[CH:18][N:17]([CH3:26])[N:16]=3)=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178448430HCID 178448430, compound

Product 1

HCID 58542030HCID 58542030, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a vial is added 5-bromo-1-tert-butyl-2-[2-(1H-[1,2,4]triazol-3-yl)-phenyl]-1H-benzimidazole (100 mg, 0.252 mmol) in DMF (1.5 mL), followed by the addition of K2CO3 (70 mg, 0.504 mmol) and MeI (60 mg, 0.423 mmol). The reaction mixture is stirred at room temperature for 1 hour. The reaction mixture is diluted with EtOAc, washed with water, brine, dried using anhydrous Na2SO4 and filtered. The filtrate is concentrated and the residue is purified by silica gel flash column chromatography with 0-3% 7M NH3 in MeOH/CH2Cl2 as the eluent to afford 5-bromo-1-tert-butyl-2-[2-(1-methyl-1H-[1,2,4]-triazol-3-yl)-phenyl]-1H-benzimidazole (37 mg, 36%) as a light brown solid. LCMS (ESMS): m/z 410.58, 412.51 (M++1)

Workup

  1. washwashed with water, brine
  2. customdried
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated
  5. customthe residue is purified by silica gel flash column chromatography with 0-3% 7M NH3 in MeOH/CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-88d965ba7ba142a98fc1171697858537
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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