Ethanol → 3-(5-(Tert-butylcarbamoyl)-4-formylthiophen-2-yl)-4-methylbenzoic acid

HRID 19580

Reaktionsgleichung

Reaktionsgleichung von HRID 19580
[C:1]([NH:5][C:6]([C:8]1[S:9][C:10](Cl)=[CH:11][C:12]=1[CH:13]=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][C:18]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+].CCO>COCCOC.[NH4+].[Cl-].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:1]([NH:5][C:6]([C:8]1[S:9][C:10]([C:18]2[CH:19]=[C:20]([CH:24]=[CH:25][C:17]=2[CH3:16])[C:21]([OH:23])=[O:22])=[CH:11][C:12]=1[CH:13]=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

9

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 160860864-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acidHCID 86618194N-tert-butyl-5-chloro-3-formylthiophene-2-carboxamide

Produkt 1

HCID 866181953-(5-(Tert-butylcarbamoyl)-4-formylthiophen-2-yl)-4-methylbenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

A mixture of N-tert-butyl-5-chloro-3-formylthiophene-2-carboxamide (2.40 g, 9.77 mmol), 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (3.07 g, 11.7 mmol), Pd(PPh3)2Cl2 (0.343 g, 0.488 mmol, Strem), and sodium carbonate (3.11 g, 29.3 mmol) in DME:EtOH:H2O=7:2:3 (36 ml) was heated to 80° C. for 8 hrs. After cooling to RT, the mixture was diluted with sat. aq. NH4Cl and extracted with EtOAc (3×). The combined organics were dried over Na2SO4, filtered and concentrated over SiO2. Column chromatography (MeOH/CH2Cl2=0→2%) gave the desired product. Yield: 2.31 g.

Aufarbeitung

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated over SiO2

Quellen und Nachweise

ORD-Eintrag
ord-b133b37652714a72aab5df9f27049a73
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745449B2

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