Dimethylformamide → HCID 117660496, compound

HRID 1428395Notes

Reaction equation

HRID 1428395 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[NH:6][C:7]([CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[N:8][C:4]=2[CH:3]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+].Cl[CH2:33][O:34][CH3:35]>CCOC(C)=O>[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]([CH2:33][O:34][CH3:35])[C:7]([CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 178483005HCID 178483005, compound

Product 1

HCID 117660496HCID 117660496, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of tert-butyl [(5-bromo-1H-benzimidazol-2-yl)methyl]methylcarbamate (1.54 g) and DMF (20 mL) were added K2CO3 (1.88 g) and chloromethylmethyl ether (516 μL) under ice-cooling, followed by stirring at room temperature overnight. The reaction mixture was diluted with EtOAc, and washed with water and brine in this order. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: Hex/EtOAc=80/20-55/45) to obtain a mixture (1.25 g) of tert-butyl {[5-bromo-1-(methoxymethyl)-1H-benzimidazol-2-yl]methyl}methylcarbamate and tert-butyl {[6-bromo-1-(methoxymethyl)-1H-benzimidazol-2-yl]methyl}methylcarbamate.

Workup

  1. temperaturecooling
  2. washwashed with water and brine in this order
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: Hex/EtOAc=80/20-55/45)

Sources & evidence

ORD record
ord-c131628f30d74deb98df9fd08e056706
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

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