Bromotrimethylsilane → {5-[1-Benzyl-6-chloro-5-(4-cyclohexyl-phenyl)-1H-benzoimidazol-2-yloxy]-2-methyl-phenyl}-phosphonic acid

HRID 1960156Notes

Reaction equation

HRID 1960156 reaction equation
C([O:3][P:4]([C:9]1[CH:14]=[C:13]([O:15][C:16]2[N:20]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:19]3[CH:28]=[C:29]([Cl:44])[C:30]([C:32]4[CH:37]=[CH:36][C:35]([CH:38]5[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]5)=[CH:34][CH:33]=4)=[CH:31][C:18]=3[N:17]=2)[CH:12]=[CH:11][C:10]=1[CH3:45])(=[O:8])[O:5]CC)C.Br[Si](C)(C)C>ClCCl.C[Si](C)(C)N[Si](C)(C)C>[CH2:21]([N:20]1[C:19]2[CH:28]=[C:29]([Cl:44])[C:30]([C:32]3[CH:33]=[CH:34][C:35]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)=[CH:36][CH:37]=3)=[CH:31][C:18]=2[N:17]=[C:16]1[O:15][C:13]1[CH:12]=[CH:11][C:10]([CH3:45])=[C:9]([P:4](=[O:3])([OH:8])[OH:5])[CH:14]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86761794{5-[1-Benzyl-6-chloro-5-(4-cyclohexyl-phenyl)-1H-benzoimidazol-2-yloxy]-2-methyl-phenyl}-phosphonic acid diethyl ester

Product 1

HCID 67377630{5-[1-Benzyl-6-chloro-5-(4-cyclohexyl-phenyl)-1H-benzoimidazol-2-yloxy]-2-methyl-phenyl}-phosphonic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13838HexamethyldisilazaneSolvent

Procedure

To a solution of {5-[1-Benzyl-6-chloro-5-(4-cyclohexyl-phenyl)-1H-benzoimidazol-2-yloxy]-2-methyl-phenyl}-phosphonic acid diethyl ester (3.2 g, 5.0 mmol) in dichloromethane (15 ml) and hexamethyldisilazane (15 ml) was added bromotrimethylsilane (7.7 ml, 50 mmol). After stirring over night at rt the volatiles were removed from the mixture on a rotary evaporator. The residue was dissolved in methanol (15 ml) and treated with sonication in a water bath. The resulting suspension was filtered to yield a white solid. This solid was dried under vacuum at 40° C. for 15 hours to yield the title compound. The filtrate was evaporated to dryness, treated with hexanes (15 ml) and subjected to sonication in a water bath. The beige solid thus obtained upon filtration was dried under vacuum at 40° C. for 15 hours to yield additional title compound in sufficient purity.

Workup

  1. customwere removed from the mixture on a rotary evaporator
  2. dissolutionThe residue was dissolved in methanol (15 ml)
  3. additiontreated with sonication in a water bath
  4. filtrationThe resulting suspension was filtered
  5. customto yield a white solid
  6. customThis solid was dried under vacuum at 40° C. for 15 hours

Sources & evidence

ORD record
ord-4ae210dbe6c5407791744650c325ffdd
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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