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Dimethylformamide → methyl 1-(4-chlorobenzyl)-4-phenyl-1H-pyrrole-2-carboxylate

HRID 1909887
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1909887
Br[C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[N:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH:6]=1.CN(C=O)C.[C:24]1(OB(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(OCC)(=O)C>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][N:5]2[CH:6]=[C:2]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:3]=[C:4]2[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:10]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 58306731methyl 4-bromo-1-(4-chlorobenzyl)-1H-pyrrole-2-carboxylate

Produkt 1

HCID 58306767methyl 1-(4-chlorobenzyl)-4-phenyl-1H-pyrrole-2-carboxylateAusbeute 36,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysator
HCID 962WaterLösungsmittel2×
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of methyl 4-bromo-1-(4-chlorobenzyl)-1H-pyrrole-2-carboxylate (0.72 g) and DMF (21 mL) were added phenylboric acid (0.30 g), sodium carbonate (0.58 g), water (3.0 mL), and tetrakis(triphenylphosphine) palladium (0.13 g), followed by stirring at 100° C. for 24 hours. To the reaction mixture were added ethyl acetate and water, and the insoluble materials were separated by filtration through Celite. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=0 to 10%) to obtain methyl 1-(4-chlorobenzyl)-4-phenyl-1H-pyrrole-2-carboxylate (0.26 g).

Aufarbeitung

  1. customthe insoluble materials were separated by filtration through Celite
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=0 to 10%)

Quellen und Nachweise

ORD-Eintrag
ord-41c9e67cb03f47c0b0d706c6b2563bd7
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08598355B2

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