Cesium carbonate → N-tert-butyl-2-(methyl(pyridin-3-yl)amino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 522986

Reaktionsgleichung

Reaktionsgleichung von HRID 522986
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:9][N:8]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:5]2=[N:6][CH:7]=1.[CH3:26][NH:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=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.C(=O)([O-])[O-].[Cs+].[Cs+]>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]>[C:14]([NH:13][C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([N:27]([CH3:26])[C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)[N:3]=2)[N:8]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH:9]=1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 140376N-Methyl-3-pyridinamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 715756452-bromo-N-(tert-butyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Produkt 1

HCID 90041212N-tert-butyl-2-(methyl(pyridin-3-yl)amino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (125 mg, 292 μmol), N-methylpyridin-3-amine (47.4 mg, 439 μmol), xantphos (50.8 mg, 87.7 μmol), Pd2(dba)3 (26.8 mg, 29.2 μmol) and cesium carbonate (191 mg, 585 μmol) in dioxane (2 mL) was heated in a microwave at 150° C. for 20 min. The mixture was cooled and then filtered through a pad of celite. The filtrate was concentrated in vacuo then purified by chromatography (silica, ethyl acetate in hexanes) to give N-tert-butyl-2-(methyl(pyridin-3-yl)amino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (38 mg, 83.6 μmol, 29%) as a yellow gum. (EI/CI) m/z: 455.4 [M+H].

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through a pad of celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthen purified by chromatography (silica, ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-79dc9df8e7b743ae89ee0b36e29d3630
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334278B2

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