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Chloroform → Ethyl 4-(4-chloro-2-methoxyphenyl)-1-methyl-1H-pyrrole-2-carboxylate

HRID 1498912
Notes
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Reaction equation

HRID 1498912 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:5]([CH3:7])[CH:6]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[C:22]([O:29][CH3:30])[CH:21]=1.C(Cl)(Cl)Cl>CN(C)C=O.O.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>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:3]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:5]([CH3:7])[CH:6]=2)=[C:22]([O:29][CH3:30])[CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 3858606(4-Chloro-2-methoxyphenyl)boronic acidHCID 72210990Ethyl 4-bromo-1-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 86679343Ethyl 4-(4-chloro-2-methoxyphenyl)-1-methyl-1H-pyrrole-2-carboxylateYield 254.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst
HCID 962WaterSolvent2×
HCID 6228DimethylformamideSolvent

Procedure

Ethyl 4-bromo-1-methyl-1H-pyrrole-2-carboxylate (5.00 g, 21.6 mmol) prepared in the Step 10-1-2 was dissolved in N,N-dimethylformamide (20 ml)/water (5 ml), and sodium carbonate (6.87 g, 64.8 mmol), tetrakis(triphenylphosphine)palladium (120 mg, 0.1 mmol) and 4-chloro-2-methoxyphenylboronic acid (8.04 g, 4.32 mmol) was added to the solution. The mixture was heated under reflux for 5 hours. After the mixture was allowed to cool, water and chloroform was added to the mixture. The organic phase was collected by separation and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3) to give the title compound (3.23 g, 51%).

Workup

  1. additionwas added to the solution
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 5 hours
  4. temperatureto cool
  5. customThe organic phase was collected by separation
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-2ac76e0536ff4802825bc8e22b0e51ae
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09200008B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes