Dichloromethane → HCID 117660503, compound

HRID 1428399Notes

Reaction equation

HRID 1428399 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[N:7]([CH2:20][O:21][CH3:22])[C:8]([CH2:10][N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[N:9][C:5]=2[CH:4]=1.COC1C=CC2N=C(CN(C)C(=O)OC(C)(C)C)N(COC)C=2C=1.ClCCl.[Br:52]N1C(=O)CCC1=O>CCOC(C)=O>[Br:52][C:24]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16])[N:7]([CH2:20][O:21][CH3:22])[C:6]=2[CH:23]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 117660501HCID 117660501, compoundHCID 117660502HCID 117660502, compound

Product 1

HCID 117660503HCID 117660503, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of a mixture (946 mg) of tert-butyl {[5-methoxy-1-(methoxymethyl)-1H-benzimidazol-2-yl]methyl}methylcarbamate and tert-butyl {[6-methoxy-1-(methoxymethyl)-1H-benzimidazol-2-yl]methyl}methylcarbamate and dichloromethane (10 mL) was added N-bromosuccinimide (527 mg) under ice-cooling, followed by stirring at room temperature overnight. The reaction mixture was diluted with EtOAc, and washed with a saturated aqueous NaHCO3 solution 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=85/15-60/40) to obtain a mixture (855 mg) of tert-butyl {[6-bromo-5-methoxy-1-(methoxymethyl)-1H-benzimidazol-2-yl]methyl}methylcarbamate and tert-butyl {[5-bromo-6-methoxy-1-(methoxymethyl)-1H-benzimidazol-2-yl]methyl}methylcarbamate.

Workup

  1. temperaturecooling
  2. washwashed with a saturated aqueous NaHCO3 solution 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=85/15-60/40)

Sources & evidence

ORD record
ord-9056916e096f444f89de5b470de782a6
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

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