Benzeneethanamine, alpha-methyl-, phosphate (1:1) → 2-fluoro-7-(2-fluoropyridin-3-yl)-3-(tributylstannyl)-5H-chromeno[2,3-b]pyridin-5-one

HRID 335906

Reaktionsgleichung

Reaktionsgleichung von HRID 335906
Br[C:2]1[CH:3]=[C:4]2[C:27](=[CH:28][CH:29]=1)[O:26][C:7]1=[N:8][C:9]([F:25])=[C:10]([Sn:12]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH2:15][CH3:16])[CH:11]=[C:6]1[C:5]2=[O:30].CC(N)CC1C=CC=CC=1.OP(O)(O)=O.C([O-])(=O)C.[K+].[F:51][C:52]1[C:57](B(O)O)=[CH:56][CH:55]=[CH:54][N:53]=1>CCO.O.C(OCC)(=O)C>[F:25][C:9]1[N:8]=[C:7]2[O:26][C:27]3[C:4]([C:5](=[O:30])[C:6]2=[CH:11][C:10]=1[Sn:12]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH2:15][CH3:16])=[CH:3][C:2]([C:57]1[C:52]([F:51])=[N:53][CH:54]=[CH:55][CH:56]=1)=[CH:29][CH:28]=3

Komponenten

8

Edukt 4

HCID 62885Benzeneethanamine, alpha-methyl-, phosphate (1:1)HCID 517044Potassium AcetateHCID 27832702-Fluoropyridine-3-boronic acidHCID 673833207-bromo-2-fluoro-3-(tributylstannyl)-5H-chromeno[2,3-b]pyridin-5-one

Produkt 1

HCID 673827952-fluoro-7-(2-fluoropyridin-3-yl)-3-(tributylstannyl)-5H-chromeno[2,3-b]pyridin-5-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

7-Bromo-2-fluoro-3-(tributylstannyl)-5H-chromeno[2,3-b]pyridin-5-one (0.240 g, 0.412 mmol), AmPhos (0.015 g, 0.021 mmol), potassium acetate (0.077 mL, 1.235 mmol), and 2-fluoro-3-pyridineboronic acid (0.070 g, 0.494 mmol) were suspended in a mixture of EtOH (20 mL) and water (2 mL) and heated to 85° C. After 30 minutes water (250 mL) and ethyl acetate (200 mL) were added and the phases mixed and separated. The organic was washed with 10% saturated sodium bicarbonate (100 mL) then dried with magnesium sulfate and evaporated to dryness under reduced pressure. The crude was purified using silica chromatography (hexane to ethyl acetate gradient) to give 2-fluoro-7-(2-fluoropyridin-3-yl)-3-(tributylstannyl)-5H-chromeno[2,3-b]pyridin-5-one.

Aufarbeitung

  1. additionthe phases mixed
  2. customseparated
  3. washThe organic was washed with 10% saturated sodium bicarbonate (100 mL)
  4. dry with materialthen dried with magnesium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe crude was purified

Quellen und Nachweise

ORD-Eintrag
ord-7adc4084163f4c1cadac176ab53a7001
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883782B2

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