Cesium carbonate → Tert-butyl 2-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamate

HRID 1844450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844450
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[N:10]=2)[CH:7]=1.[C:17](=[O:24])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[NH2:18].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)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]>[C:20]([O:19][C:17](=[O:24])[NH:18][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[N:10]=2)[CH:7]=1)([CH3:23])([CH3:22])[CH3:21]

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 717438774-(6-Bromo-[1,2,4]triazolo[1,5-A]pyridin-2-YL)morpholine

Produkt 1

HCID 89464434Tert-butyl 2-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-6-ylcarbamateAusbeute 20,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Versuchsvorschrift

A mixture of 4-(6-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)morpholine (200 mg, 706 μmol), tert-butyl carbamate (99.3 mg, 848 μmol) and cesium carbonate (322 mg, 989 μmol) was purged several times with argon, then tris(dibenzylideneacetone)dipalladium(0) (12.9 mg, 14.1 μmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (16.3 mg, 28.3 μmol) were added and the mixture was purged with argon again, the vessel was then capped. The resulting mixture was refluxed for 20 hours. The mixture was evaporated to dryness under reduced pressure. Final purification by flash chromatography (20 g silicagel column using heptane/ethyl acetate 70-100 as eluent) afforded (2-morpholin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-carbamic acid tert-butyl ester (46 mg, 20.4%) as yellow solid. Mp.: 166° C. MS: m/z=320.0 (M+H+).

Aufarbeitung

  1. customwas purged several times with argon
  2. customthe mixture was purged with argon again
  3. customthe vessel was then capped
  4. temperatureThe resulting mixture was refluxed for 20 hours
  5. customThe mixture was evaporated to dryness under reduced pressure
  6. customFinal purification by flash chromatography (20 g silicagel column using heptane/ethyl acetate 70-100 as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-3b6e91e6e15c41c3b7a1d0c079d97bc3
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946427B2

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