3-bromo-4-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine → 1H-Pyrrolo[2,3-b]pyridine, 4-chloro-3-methyl-5-phenyl-1-(phenylsulfonyl)-

HRID 79553

Reaktionsgleichung

Reaktionsgleichung von HRID 79553
[Cl-].[CH3:2][Zn+].Br[C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12]=2[Cl:14])[N:7]([S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH:6]=1>C1COCC1.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>[Cl:14][C:12]1[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][N:9]=[C:8]2[N:7]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[CH:6]=[C:5]([CH3:2])[C:13]=12

Komponenten

5

Edukt 2

HCID 687614313-bromo-4-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineHCID 178477797HCID 178477797, Verbindung

Produkt 1

HCID 687612621H-Pyrrolo[2,3-b]pyridine, 4-chloro-3-methyl-5-phenyl-1-(phenylsulfonyl)-Ausbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Methyl zinc chloride (3.35 mL, 6.70 mmol) was added to 3-bromo-4-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.00 g, 2.23 mmol) and Pd(PPh3)4 (0.129 g, 0.111 mmol) in THF (10 mL). The reaction was then heated to 80° C. for 2 hours, cooled to room temperature, and quenched with saturated NH4Cl. The resulting solids were filtered and discarded. The filtrate was diluted with DCM (500 mL) and was washed with water. The combined organic fractions were dried, filtered, and concentrated to give a crude solid that was purified by column chromatography (2:1 DCM:hexanes) to give 4-chloro-3-methyl-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.75 g, 87.7% yield).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customquenched with saturated NH4Cl
  3. filtrationThe resulting solids were filtered
  4. additionThe filtrate was diluted with DCM (500 mL)
  5. washwas washed with water
  6. customThe combined organic fractions were dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a crude solid that
  10. customwas purified by column chromatography (2:1 DCM:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-af45adbbb64e4ec3845891795d75ed55
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841304B2

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