Ethyl Acetate → methyl 5-(2-aminophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1442543

Reaktionsgleichung

Reaktionsgleichung von HRID 1442543
Br[C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[S:9][C:4]=2[C:3]=1[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.CC1(C)C(C)(C)OB([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[NH2:34])O1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>O.COCCOC.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>[NH2:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[S:9][C:4]=2[C:3]=1[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 27346522-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 58679077methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Produkt 1

HCID 58679076methyl 5-(2-aminophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (7 g, 20 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamine (4.8 g, 22 mmol), sodium hydrogen carbonate (6.7 g, 80 mmol) and tetrakis(triphenylphosphine)palladium (230 mg, 0.2 mmol) in water (20 ml) and ethylene glycol dimethyl ether (50 ml) was stirred with heating under reflux for 4 hr. The reaction mixture was cooled to room temperature and ethyl acetate (200 ml) was added. The mixture was washed successively with water (100 ml), saturated aqueous sodium hydrogen carbonate solution (100 ml) and saturated brine (100 ml), and dried over magnesium sulfate. Filtration and concentration under reduced pressure gave a crude product of methyl 5-(2-aminophenyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate. The obtained compound was used for Step 10 without purification.

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 4 hr
  3. washThe mixture was washed successively with water (100 ml), saturated aqueous sodium hydrogen carbonate solution (100 ml) and saturated brine (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and concentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5213c83512804d9ab0e83f5e35b2c222
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07659263B2

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