Sodium Carbonate → 5-(2-(4-Fluorophenyl)oxazol-4-yl)-3-methoxypyridin-2-amine

HRID 538417

Reaktionsgleichung

Reaktionsgleichung von HRID 538417
[CH3:1][O:2][C:3]1[C:4]([NH2:18])=[N:5][CH:6]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:8]=1.FC(F)(F)S(O[C:25]1[N:26]=[C:27]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[O:28][CH:29]=1)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O>[F:36][C:33]1[CH:32]=[CH:31][C:30]([C:27]2[O:28][CH:29]=[C:25]([C:7]3[CH:8]=[C:3]([O:2][CH3:1])[C:4]([NH2:18])=[N:5][CH:6]=3)[N:26]=2)=[CH:35][CH:34]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 116595992-(4-Fluorophenyl)oxazol-4-yl trifluoromethanesulfonateHCID 533980593-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Produkt 1

HCID 665905395-(2-(4-Fluorophenyl)oxazol-4-yl)-3-methoxypyridin-2-amineAusbeute 63,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (200 mg, 0.8 mmol) and 2-(4-fluorophenyl)oxazol-4-yl trifluoromethanesulfonate (250 mg, 0.8 mmol), and 2.0 M aqueous Na2CO3 (1.2 mL, 2.4 mmol) in DME (2.0 mL) was sparged with Ar. Dichlorobis(triphenylphosphine)palladium(0) (281 mg, 0.4 mmol) was added and the reaction mixture was irradiated at 150° C. for 15 min in a microwave reactor. After cooling to rt, the reaction mixture was diluted with water and extracted with EtOAc (3×). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography over (SiO2, 100:0-0:100 hexanes-EtOAc) to provide 145 mg of 5-(2-(4-fluorophenyl)oxazol-4-yl)-3-methoxypyridin-2-amine: LCMS (m/z): 286.1 (MH+), tR=0.68 min.

Aufarbeitung

  1. customwas sparged with Ar
  2. customthe reaction mixture was irradiated at 150° C. for 15 min in a microwave reactor
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography over (SiO2, 100:0-0:100 hexanes-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-87b09bd64e504677ad35b4828e23f357
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865732B2

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