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Potassium Carbonate → Methyl 4-(6-methoxypyridin-3-yl)-3,5-dimethylbenzoate

HRID 531246
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 531246
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:21])[C:11]=1B1OC(C)(C)C(C)(C)O1)[C:5]([O:7][CH3:8])=[O:6].Br[C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[N:27][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2].O1CCOCC1>[CH3:30][O:29][C:26]1[N:27]=[CH:28][C:23]([C:11]2[C:10]([CH3:21])=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=2[CH3:1])=[CH:24][CH:25]=1
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Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27348955-Bromo-2-methoxypyridineHCID 68021937Methyl 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Produkt 1

HCID 90009124Methyl 4-(6-methoxypyridin-3-yl)-3,5-dimethylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178454861
HCID 178454861, Verbindung
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Methyl 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (Step A, 2.79 g, 7.20 mmol), 1,1′-bis(di-tert-butylphoshino)ferrocene palladium dichloride (0.391 g, 0.600 mmol) and 5-bromo-2-methoxypyridine (0.776 mL, 6 mmol) were mixed in a reaction flask which was then evacuated and charged with nitrogen three times. Added 1,4-dioxane (30.0 mL) and 3.0M aqueous potassium carbonate (6.00 mL, 18.00 mmol), evacuated and charged with nitrogen (3×), then stirred overnight at 80° C. The reaction was then partitioned between ethyl acetate and water. After a second water wash, the organic was dried over sodium sulfate, filtered and evaporated. The crude was purified by silica gel chromatography, eluting with 10 column volumes of 4% ethyl acetate/hexanes followed by a gradient of 4-10% ethyl acetate/hexanes over 10 column volumes to give the title compound. 1H NMR (CDCl3, 500 MHz) δ7.94 (d, 1H), 67.79 (s, 2H), 67.36 (dd, 1H), 66.84 (d, 1H), 64.00 (s, 3H), 63.93 (s, 3H), 62.09 (s, 6H).

Aufarbeitung

  1. customwas then evacuated
  2. additioncharged with nitrogen three times
  3. additioncharged with nitrogen (3×)
  4. customThe reaction was then partitioned between ethyl acetate and water
  5. washAfter a second water wash
  6. dry with materialthe organic was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude was purified by silica gel chromatography
  10. washeluting with 10 column volumes of 4% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-6a33b7209045487d9cb1d3b95263d935
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09353101B2

Notizen zur Reaktion

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