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

HRID 1960155Notes

Reaction equation

HRID 1960155 reaction equation
[CH2:1]([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:33])[C:30](I)=[CH:31][C:18]=3[N:17]=2)[CH:12]=[CH:11][C:10]=1[CH3:34])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[CH:35]1([C:41]2[CH:46]=[CH:45][C:44](B(O)O)=[CH:43][CH:42]=2)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([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:33])[C:30]([C:38]4[CH:37]=[CH:36][C:35]([CH:41]5[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]5)=[CH:40][CH:39]=4)=[CH:31][C:18]=3[N:17]=2)[CH:12]=[CH:11][C:10]=1[CH3:34])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 45891894-Cyclohexylbenzeneboronic acidHCID 86761793[5-(1-Benzyl-6-chloro-5-iodo-1H-benzoimidazol-2-yloxy)-2-methyl-phenyl]-phosphonic acid diethyl ester

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of [5-(1-Benzyl-6-chloro-5-iodo-1H-benzoimidazol-2-yloxy)-2-methyl-phenyl]-phosphonic acid diethyl ester (5.2 g, 8.5 mmol) in toluene (30 ml) was added 4-cyclohexylbenzeneboronic acid (3.5 g, 17 mmol), tetrakis(triphenylphosphine)palladium(0) (983 mg, 0.9 mmol), and then potassium carbonate (4.7 g, 34 mmol) in a solution of H2O (15 ml). The resulting mixture was heated in a microwave reactor at 130° C. for 15 minutes, and then quenched with saturated ammonium chloride solution. The mixture was then partitioned between EtOAc and H2O. The organic layer was washed with H2O, brine, and then dried with MgSO4. The crude mixture was then purified by flash chromatography (SiO2, 80 g). The title compound was eluted with 60% EtOAc in Hexane.

Workup

  1. customquenched with saturated ammonium chloride solution
  2. customThe mixture was then partitioned between EtOAc and H2O
  3. washThe organic layer was washed with H2O, brine
  4. dry with materialdried with MgSO4
  5. customThe crude mixture was then purified by flash chromatography (SiO2, 80 g)
  6. washThe title compound was eluted with 60% EtOAc in Hexane

Sources & evidence

ORD record
ord-3c69158e61d44672b6499fdb56ede7ee
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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