Dichloromethane → HCID 67494206, Verbindung

HRID 2047190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047190
Cl[C:2]1[CH:7]=[C:6]([N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[N:5]2[N:25]=[CH:26][C:27]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:4]2[N:3]=1.CC1(C)C(C)(C)OB([C:46]2[CH2:51][CH2:50][N:49]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:48][CH:47]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl>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].O.O1CCOCC1>[CH3:14][Si:13]([CH3:16])([CH3:15])[CH2:12][CH2:11][O:10][CH2:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:6]1[N:5]2[N:25]=[CH:26][C:27]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:4]2[N:3]=[C:2]([C:46]2[CH2:51][CH2:50][N:49]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:48][CH:47]=2)[CH:7]=1

Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 86664780(5-Chloro-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-7-yl)-bis-(2-trimethylsilanyl-ethoxymethyl)-amine

Produkt 1

HCID 67494206HCID 67494206, VerbindungAusbeute 96.860,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a 40 mL scintillation vial was charged 5-chloro-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)-ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (0.86 mmol, 480 mg), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.30 mmol, 400 mg), K3PO4 (2.60 mmol, 550 mg), and PdCl2(dppf).CH2Cl2 (0.086 mmol, 70 mg). To this reaction mixture was added a 9:1 solution of 1,4-dioxane:H2O (10 mL). The vial was flushed with argon, sealed with Teflon tape, and stirred at 100° C. 18 hours. After 18 hours, the reaction was concentrated in vacuo and the residue purified via silica gel chromatography to yield tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (586 mg, 833 mmol, 97% yield) as yellow solid.

Aufarbeitung

  1. customThe vial was flushed with argon
  2. customsealed with Teflon tape
  3. custom18 hours
  4. concentrationthe reaction was concentrated in vacuo
  5. customthe residue purified via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0e04b33a54ad4d3fb21faeabfb894a57
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08591943B2

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