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Cesium fluoride → Methyl 5-methyl-2-(pyridin-2-yl)benzoate

HRID 60907
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 60907
Br[C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([Sn](CCCC)(CCCC)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)CCC.[F-].[Cs+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:12][C:9]1[CH:10]=[CH:11][C:2]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 25953Cesium fluorideHCID 6077842-(Tributylstannyl)pyridineHCID 15110996Methyl 2-bromo-5-methylbenzoate

Produkt 1

HCID 67982793Methyl 5-methyl-2-(pyridin-2-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator
HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of methyl 2-bromo-5-methylbenzoate (0.629 g, 2.747 mmol), 2-(tributylstannyl)pyridine (1.32 g, 3.585 mmol), CsF (0.834 g, 5.494 mmol), Pd(PPh3)4 (0.4 g, 0.27 mmol), and CuI (0.105 g, 0.549 mmol) in DMF (20 mL) was degassed for 10 min and then heated in the microwave reactor for 30 min at 130° C. The mixture was cooled and the solvent was removed in vacuo. The crude was dissolved with EtOAc and then washed with saturated NaHCO3 and dried over Na2SO4. The solvent was removed in vacuo to obtain the crude, which was purified by silica gel to obtain the title compound. ESI-MS (m/z): 228 [M+1]+.

Aufarbeitung

  1. customwas degassed for 10 min
  2. temperatureThe mixture was cooled
  3. customthe solvent was removed in vacuo
  4. dissolutionThe crude was dissolved with EtOAc
  5. washwashed with saturated NaHCO3
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed in vacuo
  8. customto obtain the crude, which
  9. customwas purified by silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f5515e795507478b88057ba06393f836
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09440982B2

Notizen zur Reaktion

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