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1,2-Dimethoxyethane → HCID 15947801, compound

HRID 1673019
Notes
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Reaction equation

HRID 1673019 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:19]2[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:26])[N:9]([C:11]2[CH:16]=[CH:15][C:14](Br)=[CH:13][C:12]=2[Cl:18])[CH:10]=1)=[O:5])[CH3:2].[CH3:27][S:28]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)(=[O:30])=[O:29].C([O-])([O-])=O.[K+].[K+].COCCOC>CCOC(C)=O.O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:19]2[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:26])[N:9]([C:11]2[CH:16]=[CH:15][C:14]([C:35]3[CH:34]=[CH:33][CH:32]=[C:31]([S:28]([CH3:27])(=[O:30])=[O:29])[CH:36]=3)=[CH:13][C:12]=2[Cl:18])[CH:10]=1)=[O:5])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 592404041-(4-Bromo-2-chloro-phenyl)-2-(2,6-dichloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester

Product 1

HCID 15947801HCID 15947801, compoundYield 79%

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a 2 L round bottom flask attached with condenser column and magnetic stir bar was added 1-(4-Bromo-2-chloro-phenyl)-2-(2,6-dichloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester (21.1 g, 44.5 mmol), 3-methylsulfonylphenyl boronic acid (9.78 g, 48.9 mmol), PdCl2dppf (1.09 g, 3 mol %), K2CO3 (18.9 g, 137 mmol), 1,2-dimethoxyethane (250 mL) and H2O (50 mL). The reaction solution was allowed to stir at 80° C. for 2.5 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 separatory funnel and washed with aq NH4Cl (300 mL) and aq NaCl (200 mL). The organic phase was dried over Na2SO4, filtered, concentrated on the rotavapor and chromatographed through a 300 g SiO2 column using a mobile phase gradient of 3% EtOAc to 100% EtOAc to afford 19.3 g (79% yield) of the title compound. MS (ESI) 549.3, 551.3, 553.3 [M+H]+.

Workup

  1. customTo a 2 L round bottom flask attached with condenser
  2. filtrationfiltered through a Celite
  3. customto remove
  4. customThe filtrate was transferred to a separatory funnel
  5. washwashed with aq NH4Cl (300 mL) and aq NaCl (200 mL)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated on the rotavapor
  9. customchromatographed through a 300 g SiO2 column

Sources & evidence

ORD record
ord-6a5cb4977c2b4ed09537eab6db91c0b3
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07998995B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes