1,2-Dimethoxyethane → HCID 59251220, compound

HRID 1466439Notes

Reaction equation

HRID 1466439 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([OH:16])([CH3:15])[CH3:14])[N:10]=[C:9]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[CH:4][CH:3]=1.[CH3:24][O:25][C:26]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)=[O:27].C([O-])([O-])=O.[K+].[K+].COCCOC>CCOC(C)=O.O>[CH3:24][O:25][C:26]([C:28]1[CH:33]=[C:32]([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH:12]=[C:11]([C:13]([OH:16])([CH3:15])[CH3:14])[N:10]=[C:9]3[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[CH:4][CH:3]=2)[CH:31]=[CH:30][CH:29]=1)=[O:27]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 59251547HCID 59251547, compound

Product 1

HCID 59251220HCID 59251220, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a 50 mL round bottom flask attached with Vigreux column and magnetic stir bar was added 2-[1-(4-Bromo-phenyl)-2-(2-chloro-phenyl)-1H-imidazol-4-yl]-propan-2-ol (275 mg, 702 μmol), 3-methoxycarbonylphenyl boronic acid (164 mg, 913 μmol), PdCl2dppf (51 mg, 10 mol %), K2CO3 (290 mg, 2.11 mmol), 1,2-dimethoxyethane (13 mL) and H2O (1.5 mL). The reaction solution was allowed to stir at 70° C. for approximately 2 hrs. The reaction solution was diluted with EtOAc (150 mL) and filtered through a Celite padded Buchner funnel to remove spent Pd. The filtrate was transferred to a reparatory funnel and washed with aq NH4Cl (100 mL) and aq NaCl (100 mL). The organic phase was dried over Na2SO4, filtered, concentrated on the Rotavapor and chromatographed through a 25 g SiO2 column using a mobile phase gradient of 100% Hx to 90% EtOAc to afford 122 mg (39% yield) of product MS (ES): 446.3, 448.3 [M+H]+.

Workup

  1. customTo a 50 mL round bottom flask attached with Vigreux column and magnetic stir bar
  2. filtrationfiltered through a Celite
  3. customto remove
  4. customThe filtrate was transferred to a reparatory funnel
  5. washwashed with aq NH4Cl (100 mL) and aq NaCl (100 mL)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated on the Rotavapor
  9. customchromatographed through a 25 g SiO2 column

Sources & evidence

ORD record
ord-96557e6e8c29483cb559e9b36bbc6783
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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