1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → tert-butyl N-[1-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]-6-methyl-3-piperidyl]carbamate

HRID 57878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57878
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][NH:10][C:4]=2[CH:3]=1.Br[C:12]1[N:17]=[C:16]([N:18]2[CH:23]([CH3:24])[CH2:22][CH2:21][CH:20]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:19]2)[CH:15]=[CH:14][CH:13]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:12]3[N:17]=[C:16]([N:18]4[CH:23]([CH3:24])[CH2:22][CH2:21][CH:20]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:19]4)[CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1

Komponenten

7

Edukt 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 569321096-Chloro-1H-pyrazolo(4,3-c)pyridineHCID 86707072tert-butyl N-[1-(6-bromo-2-pyridyl)-6-methyl-3-piperidyl]carbamate

Produkt 1

HCID 86707073tert-butyl N-[1-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]-6-methyl-3-piperidyl]carbamateAusbeute 64,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 6-chloro-1H-pyrazolo[4,3-c]pyridine (100 mg, 0.651 mmol), tert-butyl N-[1-(6-bromo-2-pyridyl)-6-methyl-3-piperidyl]carbamate (422 mg, 1.14 mmol), tris(dibenzylideneacetone)dipalladium(0) (59 mg, 0.065 mmol), xantphos (78 mg, 0.130 mmol), and sodium tert-butoxide (129 mg, 1.30 mmol) in toluene 6.0 mL was stirred at 100° C. 18 h. The reaction was filtered through celite. The crude product was purified by flash chromatography (EtOAc/Heptane) to give the desired product (185 mg) in 64% yield. MS (ESI) m/z: 443.2

Aufarbeitung

  1. custom18 h
  2. filtrationThe reaction was filtered through celite
  3. customThe crude product was purified by flash chromatography (EtOAc/Heptane)

Quellen und Nachweise

ORD-Eintrag
ord-8b698e1bde0a4e9b930a04601eaeb240
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

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