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Sodium Carbonate → 5-(2-(4-Aminophenoxy)pyridin-3-yl)thiazol-2-amine

HRID 593950
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 593950
CC1(C)C(C)(C)OB([C:9]2[C:10]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)=[N:11][CH:12]=[CH:13][CH:14]=2)O1.Br.Br[C:26]1[S:30][C:29]([NH2:31])=[N:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>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].O1CCOCC1>[NH2:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][C:10]2[C:9]([C:26]3[S:30][C:29]([NH2:31])=[N:28][CH:27]=3)=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:21][CH:20]=1
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Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 27238485-Bromothiazol-2-amine monohydrobromideHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 574164444-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yloxy)benzenamine

Produkt 1

HCID 577562445-(2-(4-Aminophenoxy)pyridin-3-yl)thiazol-2-amine

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a 20 mL sealed tube was added dioxane (1.0 mL), purged solvent with nitrogen for 5 minutes and the tube was sealed. 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yloxy)benzenamine (0.144 g, 0.462 mmol), 5-bromothiazol-2-amine hydrobromide (0.100 g, 0.385 mmol), 2.0M aqueous sodium carbonate (0.385 mL) was added and the tube was purged flask with nitrogen, and again sealed. Tris(dibenzylideneacetone)dipalladium (0) (0.026 g, 0.029 mmol), tri-t-butylphosphonium tetrafluoroborate (0.025 g, 0.087 mmol) was added and the tube was purged with nitrogen, sealed and heated to 100° C. while stirring for 5 hours. The mixture was cooled to RT, passed through pad of silica, washing with 90:10:1 (CH2Cl2: MeOH: NH4OH). The eluent was concentrated and the product was purified by silica gel chromatography eluting with 0-100% CH2Cl2:MeOH(90:10)/CH2Cl2. The product fractions were concentrated to yield 5-(2-(4-aminophenoxy)pyridin-3-yl)thiazol-2-amine as tan solid. MS m/z=285 [M+1]+. Calc'd for C14H12N4OS: 284.34.

Aufarbeitung

  1. customIn a 20 mL sealed tube
  2. custompurged solvent with nitrogen for 5 minutes
  3. customthe tube was sealed
  4. customthe tube was purged flask with nitrogen
  5. customagain sealed
  6. customthe tube was purged with nitrogen
  7. customsealed
  8. temperatureThe mixture was cooled to RT
  9. washwashing with 90:10:1 (CH2Cl2: MeOH: NH4OH)
  10. concentrationThe eluent was concentrated
  11. customthe product was purified by silica gel chromatography
  12. washeluting with 0-100% CH2Cl2:MeOH(90:10)/CH2Cl2
  13. concentrationThe product fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-f58ba438011d4c15b65771985290af52
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242961B2

Notizen zur Reaktion

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