Sodium hydride → 1-Biphenyl-4-ylmethyl-6-chloro-5-iodo-2-methanesulfonyl-1H-benzoimidazole

HRID 1960150Notes

Reaction equation

HRID 1960150 reaction equation
[Cl:1][C:2]1[C:3]([I:15])=[CH:4][C:5]2[N:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[NH:7][C:6]=2[CH:14]=1.[H-].[Na+].Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:22][CH:21]=1>CN(C=O)C>[C:23]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:22]=[CH:21][C:20]([CH2:19][N:7]2[C:6]3[CH:14]=[C:2]([Cl:1])[C:3]([I:15])=[CH:4][C:5]=3[N:9]=[C:8]2[S:10]([CH3:13])(=[O:12])=[O:11])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2577161,1'-Biphenyl, 4-(bromomethyl)-HCID 574814665-chloro-6-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole

Product 1

HCID 673776421-Biphenyl-4-ylmethyl-6-chloro-5-iodo-2-methanesulfonyl-1H-benzoimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-chloro-5-iodo-2-methanesulfonyl-1H-benzoimidazole (1.53 g, 4.3 mmol) in DMF (21 ml) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 190 mg, 4.7 mmol). After 15 minutes, the reaction was warmed to rt and stirred for 1 hour. The mixture was then cooled to 0° C. and 4-bromomethyl-biphenyl (1.2 g, 4.7 mmol) was slowly added. The mixture was then warmed to rt and stirred overnight. The volatiles were removed on a rotary evaporator and the residue was partitioned between EtOAc and half-saturated ammonium chloride. The aqueous layer was extracted a second time and the organic extracts were combined. The combined EtOAc extracts were washed with H2O, brine, and then dried with MgSO4. The crude oil obtained upon rotary evaporation was triturated in Et2O and filtered to yield the title compound as a beige solid.

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. temperatureThe mixture was then warmed to rt
  3. stirringstirred overnight
  4. customThe volatiles were removed on a rotary evaporator
  5. customthe residue was partitioned between EtOAc and half-saturated ammonium chloride
  6. extractionThe aqueous layer was extracted a second time
  7. washThe combined EtOAc extracts were washed with H2O, brine
  8. dry with materialdried with MgSO4
  9. customThe crude oil obtained upon rotary evaporation
  10. customwas triturated in Et2O
  11. filtrationfiltered

Sources & evidence

ORD record
ord-5ae878de6fd142ec9be64bf5a14264c8
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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