Triethylamine → 7-chloro-2-((1-(4-methoxybenzyl)-5-(pyrrolidin-1-yl)-1H-1,2,4-triazol-3-yl)ethynyl)quinoxaline

HRID 1055028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1055028
[C:1]([C:3]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[N:5]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:4]=1)#[CH:2].Cl[C:23]1[CH:32]=[N:31][C:30]2[C:25](=[CH:26][C:27]([Cl:33])=[CH:28][CH:29]=2)[N:24]=1.C(N(CC)CC)C>O1CCCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:33][C:27]1[CH:26]=[C:25]2[C:30]([N:31]=[CH:32][C:23]([C:2]#[C:1][C:3]3[N:7]=[C:6]([N:8]4[CH2:12][CH2:11][CH2:10][CH2:9]4)[N:5]([CH2:13][C:14]4[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=4)[N:4]=3)=[N:24]2)=[CH:29][CH:28]=1

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 27582232,7-DichloroquinoxalineHCID 900255173-ethynyl-1-(4-methoxy-benzyl)-5-pyrrolidin-1-yl-1H-[1,2,4]triazole

Produkt 1

HCID 900174367-chloro-2-((1-(4-methoxybenzyl)-5-(pyrrolidin-1-yl)-1H-1,2,4-triazol-3-yl)ethynyl)quinoxalineAusbeute 49,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11776TriphenylphosphineKatalysatorHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 3-ethynyl-1-(4-methoxybenzyl)-5-(pyrrolidin-1-yl)-1H-1,2,4-triazole (115 mg, 407 μmol, Eq: 1.00), 2,7-dichloroquinoxaline (89.2 mg, 448 μmol, Eq: 1.1) and triethylamine (61.8 mg, 85.2 μl, 611 μmol, Eq: 1.5) in tetrahydrofuran (3 ml) was purged with argon, then copper (I) iodide (3.1 mg, 16.3 μmol, Eq: 0.04), bis(triphenylphosphine)palladium(II) chloride (11.4 mg, 16.3 μmol, Eq: 0.04) and triphenylphosphine (4.27 mg, 16.3 μmol, Eq: 0.04) were added, the vessel was capped and heated for 18 hours to 75° C. The crude material was applied on silica gel and purified by flash chromatography to give 7-Chloro-2-[1-(4-methoxy-benzyl)-5-pyrrolidin-1-yl-1H-[1,2,4]triazol-3-ylethynyl]-quinoxaline (89 mg, 49.1%) as yellow solid. MS: m/z=445.4 (M+H+)

Aufarbeitung

  1. customwas purged with argon
  2. customthe vessel was capped
  3. temperatureheated for 18 hours to 75° C
  4. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-082ba8a0c9924900b87effe9fef59afd
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394311B2

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