Potassium Carbonate → methyl N-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)-2-pyrrolecarboxylate

HRID 1130

Reaction equation

HRID 1130 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5](I)[CH:4]=[C:3]1[C:8]([O:10][CH3:11])=[O:9].[CH3:12][C:13]1([CH3:32])[CH2:26][CH2:25][C:24]([CH3:28])([CH3:27])[C:23]2[CH:22]=[C:21]3[C:16]([CH:17]=[CH:18][C:19](B(O)O)=[CH:20]3)=[CH:15][C:14]1=2.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[C:5]([C:19]2[CH:18]=[CH:17][C:16]3[C:21](=[CH:22][C:23]4[C:24]([CH3:28])([CH3:27])[CH2:25][CH2:26][C:13]([CH3:32])([CH3:12])[C:14]=4[CH:15]=3)[CH:20]=2)[CH:4]=[C:3]1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 196946765,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-anthrylboronic acidHCID 21826247methyl 4-iodo-1-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 19694675methyl N-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)-2-pyrrolecarboxylateYield 47%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

231 mg (0.2 mml) of tetrakis-(triphenylphosphine)palladium (0), 50 ml of toluene and 1.75 g (6.6 mmol) of methyl N-methyl-4-iodo-2-pyrrolecarboxylate were introduced into a three-necked flask and under a nitrogen stream and the mixture was stirred at room temperature for 20 minutes. 2.8 g (10 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthrylboronic acid and 6.6 ml of an aqueous potassium carbonate solution (2N) were then added and the mixture was heated at reflux for 8 hours. The reaction medium was evaporated to dryness, taken up in water and ethyl ether, the organic phase decanted, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a silica column eluted with a mixture of dichloromethane and hexane (80/20). 840 mg (47%) of methyl N-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)-2-pyrrolecarboxylate were obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 8 hours
  3. customThe reaction medium was evaporated to dryness
  4. customethyl ether, the organic phase decanted
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by chromatography on a silica column
  8. washeluted with a mixture of dichloromethane and hexane (80/20)

Sources & evidence

ORD record
ord-205c29c6463642c4a3ef2726db5ff6fc
Source dataset
uspto-grants-1998_03
Patent number
US05723499

Linked notes

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