Sodium Bicarbonate → tert-butyl 4-(6-(6-(pyrimidin-5-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

HRID 57881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57881
Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[N:16]=[C:15]([N:17]4[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19][CH2:18]4)[CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.[N:31]1[CH:36]=[C:35](B(O)O)[CH:34]=[N:33][CH:32]=1.C([O-])(O)=O.[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:31]1[CH:36]=[C:35]([C:2]2[N:7]=[CH:6][C:5]3[CH:8]=[N:9][N:10]([C:11]4[N:16]=[C:15]([N:17]5[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])[CH2:19][CH2:18]5)[CH:14]=[CH:13][CH:12]=4)[C:4]=3[CH:3]=2)[CH:34]=[N:33][CH:32]=1

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 86707047tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

Produkt 1

HCID 86707075tert-butyl 4-(6-(6-(pyrimidin-5-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylateAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate (427 mg, 1.0 mmol), pyrimidin-5-ylboronic acid (372 mg, 3.0 mmol), PdCl2(dppf) (73 mg, 0.1 mmol), and aq. Solution of NaHCO3 (318 mg, 3.0 mmol) in 1,4-dioxane (5.0 mL) in a sealed tube was purged with nitrogen and stirred at 100° C. for 16 hours. After it was cooled to room temperature, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography using petroleum ether:EtOAc (5:1˜1:1) as eluting solvents to afford tert-butyl 4-(6-(6-(pyrimidin-5-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate as yellow solid (350 mg, yield 74%). ESI (MS) m/z=473 [M+H]+

Aufarbeitung

  1. customwas purged with nitrogen
  2. temperatureAfter it was cooled to room temperature
  3. filtrationthe reaction mixture was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe crude product was purified by silica gel chromatography
  6. washas eluting solvents

Quellen und Nachweise

ORD-Eintrag
ord-aedfc36367e649c89823fd156323e1da
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

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