Cesium carbonate → HCID 86606576, Verbindung

HRID 2244453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244453
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[N:12]=[C:13]([CH3:17])[S:14][C:15]=2[NH2:16])=[O:10])[CH:5]=[CH:4][N:3]=1.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.Br[C:61]1[CH:62]=[N:63][CH:64]=[C:65]([C:67]([F:70])([F:69])[F:68])[CH:66]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O1CCOCC1>[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[N:12]=[C:13]([CH3:17])[S:14][C:15]=2[NH:16][C:61]2[CH:62]=[N:63][CH:64]=[C:65]([C:67]([F:70])([F:69])[F:68])[CH:66]=2)=[O:10])[CH:5]=[CH:4][N:3]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 111279913-Bromo-5-(trifluoromethyl)pyridineHCID 866065745-Amino-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide

Produkt 1

HCID 86606576HCID 86606576, VerbindungAusbeute 46,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A microwave vial was charged with 5-amino-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide (0.200 g, 0.806 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (0.159 g, 0.275 mmol) and palladium dibenzylideneacetone (Pd2dba3)-chloroform complex (0.086 g, 0.083 mmol). Degassed dioxane (10 ml) was added, followed by 3-bromo-5-(trifluoromethyl)pyridine (0.223 g, 0.991 mmol) and cesium carbonate (0.527 g, 1.62 mmol) The vial was then irradiated in a microwave oven at 150° C. for 90 min. The mixture was diluted with THF and the solids filtered, washing with THF. The filtrate was evaporated and the residue purified by flash chromatography on silica gel with dichloromethane/methanol 100:0→90:10 gradient to yield the title compound (0.147 g, 46%) as an off-white solid, MS (ISP): m/e=394.0 (M+H+).

Aufarbeitung

  1. customwas then irradiated in a microwave oven at 150° C. for 90 min
  2. filtrationthe solids filtered
  3. washwashing with THF
  4. customThe filtrate was evaporated
  5. customthe residue purified by flash chromatography on silica gel with dichloromethane/methanol 100:0→90:10 gradient

Quellen und Nachweise

ORD-Eintrag
ord-0e16a9817f42407fb9b3c70f3e08fec8
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678815B2

Notizen zur Reaktion

Wird geladen…