Potassium Carbonate → [5-(1-Benzyl-6-chloro-5-iodo-1H-benzoimidazol-2-yloxy)-2-methyl-phenyl]-phosphonic acid diethyl ester

HRID 1960154Notes

Reaction equation

HRID 1960154 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([Cl:18])[C:15]([I:17])=[CH:16][C:11]=2[N:10]=[C:9]1S(C)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([O:25][P:26]([C:31]1[CH:36]=[C:35]([OH:37])[CH:34]=[CH:33][C:32]=1[CH3:38])(=[O:30])[O:27][CH2:28][CH3:29])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:28]([O:27][P:26]([C:31]1[CH:36]=[C:35]([O:37][C:9]2[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:12]3[CH:13]=[C:14]([Cl:18])[C:15]([I:17])=[CH:16][C:11]=3[N:10]=2)[CH:34]=[CH:33][C:32]=1[CH3:38])(=[O:30])[O:25][CH2:23][CH3:24])[CH3:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57481474Diethyl 5-hydroxy-2-methylphenylphosphonateHCID 674461461-Benzyl-6-chloro-5-iodo-2-methanesulfonyl-1H-benzoimidazole

Product 1

HCID 86761793[5-(1-Benzyl-6-chloro-5-iodo-1H-benzoimidazol-2-yloxy)-2-methyl-phenyl]-phosphonic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-benzyl-6-chloro-5-iodo-2-methanesulfonyl-1H-benzoimidazole (2.7 g, 6.0 mmol) in DMF (30 ml) was added (5-hydroxy-2-methyl-phenyl)-phosphonic acid diethyl ester (1.9 g, 8.4 mmol), followed by potassium carbonate (1.7 g, 12 mmol). After stirring overnight at rt the volatiles were removed by rotary evaporation. The residue thus obtained was partitioned between EtOAc and half-saturated ammonium chloride solution. The EtOAc layer was washed with H2O, brine, and then dried with MgSO4. The crude oil was then purified by flash chromatrography (SiO2, 80 g) using a gradient up to 65% EtOAc in hexane to yield the title compound.

Workup

  1. customwere removed by rotary evaporation
  2. customThe residue thus obtained
  3. customwas partitioned between EtOAc and half-saturated ammonium chloride solution
  4. washThe EtOAc layer was washed with H2O, brine
  5. dry with materialdried with MgSO4
  6. customThe crude oil was then purified by flash chromatrography (SiO2, 80 g)

Sources & evidence

ORD record
ord-bf254ef767b24e67b28d758056d59f1f
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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