2-Bromo-6-(pyrrolidin-1-yl)pyridine → 2,2-dimethyl-1-[2-(6-pyrrolidin-1-yl-pyridin-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one

HRID 2079842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2079842
[CH3:1][C:2]([CH3:28])([CH3:27])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([Sn](CCCC)(CCCC)CCCC)[N:12]=2)[NH:7][CH:6]=1)=[O:4].Br[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([N:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)[N:31]=1>O1CCOCC1.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>[CH3:28][C:2]([CH3:1])([CH3:27])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([N:36]4[CH2:40][CH2:39][CH2:38][CH2:37]4)[N:31]=3)[N:12]=2)[NH:7][CH:6]=1)=[O:4]

Komponenten

5

Edukt 2

HCID 154702772-Bromo-6-(pyrrolidin-1-yl)pyridineHCID 578292302,2-dimethyl-1-(2-tributylstannanyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-propan-1-one

Produkt 1

HCID 441925182,2-dimethyl-1-[2-(6-pyrrolidin-1-yl-pyridin-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-oneAusbeute 1,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysator2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 2,2-dimethyl-1-(2-tributylstannanyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-propan-1-one (115 mg, 0.23 mmol), 2-bromo-6-pyrrolidin-1-yl-pyridine (53 mg, 0.23 mmol), and Pd(PPh3)4 (27 mg, 0.023 mmol) in dioxane (1 mL) was stirred at 140° C. in a microwave for 1 h. The resulting mixture was treated with additional Pd(PPh3)4 (27 mg, 0.023 mmol), stirred at 150° C. in a microwave for 30 min, and concentrated. The crude product was purified by flash chromatography using 4 g of silica gel and EtOAc in hexanes as eluant, 3 consecutive purifications by preparative thin layer chromatography using 2:1 hexanes:EtOAc as eluant, and a recrystallization from CH2Cl2 and ethyl ether to provide 1.5 mg of 2,2-dimethyl-1-[2-(6-pyrrolidin-1-yl-pyridin-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one as a yellow powder. M+H 350.

Aufarbeitung

  1. stirringstirred at 150° C. in a microwave for 30 min
  2. concentrationconcentrated
  3. customThe crude product was purified by flash chromatography
  4. customEtOAc as eluant, and a recrystallization from CH2Cl2 and ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-50ef60f959674e838b8802ebdd52f8ef
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932254B2

Notizen zur Reaktion

Wird geladen…