Pyridine → HCID 66914781, compound

HRID 880428Notes

Reaction equation

HRID 880428 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8]([CH3:15])[NH:7][C:6]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8]([CH3:15])[N:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:6]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 10062362HCID 10062362, compound

Product 1

HCID 66914781HCID 66914781, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of diethyl 3-(2-methoxyethyl)-5-methyl-1H-pyrrole-2,4-dicarboxylate (100 mg, 0.35 mmol), phenyl boronic acid (130 mg, 1.06 mmol), copper acetate (130 mg, 0.71 mmol), dry pyridine (110 mg, 1.40 mmol), molecular sieves (400 mg) and dichloromethane (10 mL) was purged with argon gas for 30 min and stirred overnight. The mixture was filtered through a celite bed, washed with dichloromethane (15 mL) and concentrated under reduced pressure. The crude compound was purified by column chromatography over silica gel (100-200 mesh) using 20% ethyl acetate/pet ether as eluent to afford diethyl 3-(2-methoxyethyl)-5-methyl-1-phenyl-pyrrole-2,4-dicarboxylate (50 mg, 40%) as a colourless oil.

Workup

  1. customwas purged with argon gas for 30 min
  2. filtrationThe mixture was filtered through a celite bed
  3. washwashed with dichloromethane (15 mL)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude compound was purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-243311dacd6f4db88ee0f2e84dd3ad21
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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