1-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde → 1H-Pyrrolo[2,3-b]pyridine-3-methanol, a-cyclopropyl-1-(phenylsulfonyl)-

HRID 2196699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2196699
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[C:12]([CH:19]=[O:20])=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:21]1([Mg]Cl)[CH2:23][CH2:22]1>C1COCC1>[CH:21]1([CH:19]([C:12]2[C:13]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:8])=[O:9])[CH:11]=2)[OH:20])[CH2:23][CH2:22]1

Komponenten

4

Edukt 2

HCID 103566461-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 178478986HCID 178478986, Verbindung

Produkt 1

HCID 671557641H-Pyrrolo[2,3-b]pyridine-3-methanol, a-cyclopropyl-1-(phenylsulfonyl)-Ausbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (0.25 g, 0.87 mmol) was dissolved in dry THF (9 mL) and chilled to 0° C. Cyclopropylmagnesium chloride (2.6 mL of a 0.5M solution in THF, 1.5 eq.) was then added by syringe to the cold reaction mixture and stirred at 0° C. for 30 minutes. The mixture was then quenched with saturated ammonium chloride solution, extracted with EtOAc, extracts dried over sodium sulfate and concentrated to provide cyclopropyl(1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)methanol (0.285 g, 98%). m/z (APCI-pos) M+1=329.1.

Aufarbeitung

  1. customThe mixture was then quenched with saturated ammonium chloride solution
  2. extractionextracted with EtOAc
  3. dry with materialextracts dried over sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-29bab400bff446939511ad3f27f84817
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338452B2

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