Potassium Carbonate → 4-(3-nitro-2-methoxy-phenyl)-1-(p-tolylsulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester

HRID 384416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 384416
O1CCOCC1.[CH3:7][O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=1B1OC(C)(C)C(C)(C)O1.[CH3:27][O:28][C:29]([C:31]1[N:32]([S:37]([C:40]2[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=2)(=[O:39])=[O:38])[CH:33]=[C:34](I)[CH:35]=1)=[O:30].C(=O)([O-])[O-].[K+].[K+]>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.O>[CH3:27][O:28][C:29]([C:31]1[N:32]([S:37]([C:40]2[CH:41]=[CH:42][C:43]([CH3:46])=[CH:44][CH:45]=2)(=[O:38])=[O:39])[CH:33]=[C:34]([C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([N+:15]([O-:17])=[O:16])[C:9]=2[O:8][CH3:7])[CH:35]=1)=[O:30]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 574838002-(2-Methoxy-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 59694429Methyl 4-iodo-1-tosyl-1H-pyrrole-2-carboxylate

Produkt 1

HCID 596156904-(3-nitro-2-methoxy-phenyl)-1-(p-tolylsulfonyl)-1H-pyrrole-2-carboxylic acid methyl esterAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 15 mL of 1,4-dioxane and 5 mL of water was added 2-(2-methoxy-3-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 6a (2.05 g, 5.5 mmol) followed by 4-iodo-1-(toluene-4-sulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester 57e (2.03 g, 5 mmol), potassium carbonate (1.38 g, 10 mmol) and tetrakis(triphenylphosphine)palladium (144 mg, 0.125 mmol). Upon completion of the addition, the reaction mixture was reacted at 80° C. for 30 minutes under microwave. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure and the residue was diluted with 20 mL of water. After mixing well, the mixture was extracted with ethyl acetate (20 mL×3). The combined organic extracts were washed with saturated brine, dried over anhydrous magnesium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 4-(3-nitro-2-methoxy-phenyl)-1-(p-tolylsulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester 57f (1.04 g, yield 48%) as a grey solid.

Aufarbeitung

  1. additionUpon completion of the addition
  2. customthe reaction mixture was reacted at 80° C. for 30 minutes under microwave
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with 20 mL of water
  5. additionAfter mixing well
  6. extractionthe mixture was extracted with ethyl acetate (20 mL×3)
  7. washThe combined organic extracts were washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customto remove the drying agent
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-54c6ef53db40493d90fb9ba1dfc70a90
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367710B2

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