Cesium carbonate → [7-(2-Chloro-5-methoxy-phenyl)-6-methyl-benzo[1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

HRID 273503

Reaktionsgleichung

Reaktionsgleichung von HRID 273503
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:20]([CH3:21])=[CH:19][C:13]2[N:14]=[C:15]([NH2:18])[N:16]=[N:17][C:12]=2[CH:11]=1.Br[C:23]1[CH:36]=[CH:35][C:26]([O:27][CH2:28][CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:25][CH:24]=1.C([O-])([O-])=O.[Cs+].[Cs+].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>O1CCOCC1.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[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:20]([CH3:21])=[CH:19][C:13]2[N:14]=[C:15]([NH:18][C:23]3[CH:24]=[CH:25][C:26]([O:27][CH2:28][CH2:29][N:30]4[CH2:31][CH2:32][CH2:33][CH2:34]4)=[CH:35][CH:36]=3)[N:16]=[N:17][C:12]=2[CH:11]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 70657N-(2-(p-bromophenoxy)ethyl)pyrrolidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 689796617-(2-Chloro-5-methoxy-phenyl)-6-methyl-benzo[1,2,4]triazin-3-ylamine

Produkt 1

HCID 59837634[7-(2-Chloro-5-methoxy-phenyl)-6-methyl-benzo[1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

7-(2-chloro-5-methoxy-phenyl)-6-methyl-benzo[1,2,4]triazin-3-ylamine (0.67 mmol, 1.0 equiv), 1-[2-(4-bromophenoxy)-ethyl] pyrrolidine (0.005 mmol, 1.5 equiv), Cs2CO3 (2.01 mmol, 3.0 equiv), Pd2(dba)3 (0.067 mmol, 0.1 equiv), and Xantphos (0.134 mmol, 0.2 equiv) were dissolved in 20 mL dioxane, placed under an argon atmosphere and refluxed at 100° C. for 18 h. The reaction was cooled to room temperature and filtered. The filtrate was dissolved in EtOAc, washed with saturated NaHCO3 and brine and organic phase was dried (Na2SO4). The organics were concentrated under reduced pressure to afford residue that was precipitated out using EtOAc/hexanes (1:5 v/v) to give [7-(2 chloro-5-methoxy-phenyl)-6-methyl-benzo[1,2,4]triazin-3-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine, as an orange solid (271.2 mg, 83% yield). Rf=0.56 (9:1 DCM/MeOH). MS (ES+) m/z=491. LC retention time 2.72 min.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered
  3. dissolutionThe filtrate was dissolved in EtOAc
  4. washwashed with saturated NaHCO3 and brine and organic phase
  5. dry with materialwas dried (Na2SO4)
  6. concentrationThe organics were concentrated under reduced pressure
  7. customto afford residue
  8. customthat was precipitated out

Quellen und Nachweise

ORD-Eintrag
ord-9b9cd78048554376944da750711c46d3
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456176B2

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