Tributylphenyltin → 2-(4-Fluoro-phenyl)-4-hydroxy-1,3-diphenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642268Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 642268
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:29])=[C:8]2[C:14](Br)=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[N:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].[C:30]1([Sn](CCCC)(CCCC)CCCC)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C=O)C.CCOC(C)=O.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>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:29])=[C:8]2[C:14]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[N:12]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]

Komponenten

6

Edukt 2

HCID 607632TributylphenyltinHCID 684284133-bromo-2-(4-fluoro-phenyl)-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Produkt 1

HCID 684285202-(4-Fluoro-phenyl)-4-hydroxy-1,3-diphenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl esterAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 3-bromo-2-(4-fluoro-phenyl)-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (180 mg, 0.395 mmol), phenyltributlytin (149 μL, 0.454 mmol), and Pd(PPh3)2Cl2 (14 mg, 0.020 mmol) in DMF (2 mL) was stirred at 130° C. overnight. Then the mixture was diluted with EtOAc, washed with water and saturated NaCl aqueous solution respectively; the EtOAc phase was dried over anhydrous sodium sulfate, concentrated, the residue was purified by column and prep TLC to give a white solid, the desired title compound (59 mg). The title compound, ESI MS (m/z): 453 (M+H+).

Aufarbeitung

  1. washwashed with water and saturated NaCl aqueous solution respectively
  2. dry with materialthe EtOAc phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customthe residue was purified by column
  5. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-bdc20afe24e94f2b97a5fcd2c6f6476f
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

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