Trimethyl-(6-methylpyrazin-2-yl)stannane → tert-butyl 4-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3,6-dihydro-2H-pyridine-1-carboxylate

HRID 57862Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57862
Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[N:16]=[C:15]([C:17]4[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH:22]=4)[CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.C[Sn](C)(C)[C:32]1[CH:37]=[N:36][CH:35]=[C:34]([CH3:38])[N:33]=1>CN(C)C(=O)C>[CH3:38][C:34]1[N:33]=[C:32]([C:2]2[N:7]=[CH:6][C:5]3[CH:8]=[N:9][N:10]([C:11]4[N:16]=[C:15]([C:17]5[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])[CH2:21][CH:22]=5)[CH:14]=[CH:13][CH:12]=4)[C:4]=3[CH:3]=2)[CH:37]=[N:36][CH:35]=1

Komponenten

4

Edukt 2

HCID 86707041Trimethyl-(6-methylpyrazin-2-yl)stannaneHCID 86707057tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]-3,6-dihydro-2H-pyridine-1-carboxylate

Produkt 1

HCID 86707059tert-butyl 4-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3,6-dihydro-2H-pyridine-1-carboxylateAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

A solution of tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]-3,6-dihydro-2H-pyridine-1-carboxylate (200 mg, 0.486 mmol) and palladium(0)tetrakis(triphenylphosphine) (56 mg, 0.049 mmol) in N,N-dimethylacetamide 5.0 mL was added trimethyl-(6-methylpyrazin-2-yl)stannane (250 mg, 0.971 mmol). The reaction mixture heated at 145° C. for 40 min in microwave. The reaction mixture was filtered through celite and concentrated. The crude product was diluted with EtOAc then washed with water. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was purified by flash chromatography (EtOAc/Heptane eluted at 65% EtOAc) to give the desired product 165 mg 72% yield.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated
  3. additionThe crude product was diluted with EtOAc
  4. washthen washed with water
  5. dry with materialThe organic layers was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customThe crude product was purified by flash chromatography (EtOAc/Heptane eluted at 65% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-5992e1de3d8948f1b7c8e2be5b87529d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

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