Diethyl Ether → Tert-butyl 2-(6-chloro-5-(trifluoromethyl)pyridin-3-yl)acetate

HRID 592205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 592205
Br[C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:5]([Cl:8])=[N:6][CH:7]=1.[Cl-].[C:14]([O:18][C:19](=[O:22])[CH2:20][Zn+])([CH3:17])([CH3:16])[CH3:15].CCOCC>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].CC(P(C(C)(C)C)[C-]1C=CC=C1)(C)C.C1C=CC([C-]2C(C3C=CC=CC=3)=C(C3C=CC=CC=3)C(C3C=CC=CC=3)=C2C2C=CC=CC=2)=CC=1.[Fe+2].C1COCC1>[Cl:8][C:5]1[N:6]=[CH:7][C:2]([CH2:20][C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:22])=[CH:3][C:4]=1[C:9]([F:12])([F:11])[F:10]

Komponenten

7

Edukt 3

HCID 3283Diethyl EtherHCID 218363025-Bromo-2-chloro-3-(trifluoromethyl)pyridineHCID 178451183HCID 178451183, Verbindung

Produkt 1

HCID 86657956Tert-butyl 2-(6-chloro-5-(trifluoromethyl)pyridin-3-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 129828017Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzeneKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a sealed tube were added 5-bromo-2-chloro-3-(trifluoromethyl)pyridine 189-1 (170 mg, 0.65 mmol), 0.5 M (2-tert-butoxy-2-oxoethyl) zinc(II) chloride 86-5 in ether (1.57 mL, 0.78 mmol), Pd(dba)2 (19 mg, 0.03 mmol), Q-phos (46 mg, 0.06 mmol) and THF (3 mL). The reaction mixture was bubbled with nitrogen for 1 minute and stirred at 100° C. for 1 hour. After cooling to room temperature, all the solvents were evaporated and the residue was redissolved in ethyl acetate, washed with water and brine, dried over Na2SO4 and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography and eluted with 20% ethyl acetate in hexane to give tert-butyl 2-(6-chloro-5-(trifluoromethyl)pyridin-3-yl)acetate 189-3. MS m/z 296.1 (M+1).

Aufarbeitung

  1. customThe reaction mixture was bubbled with nitrogen for 1 minute
  2. temperatureAfter cooling to room temperature
  3. customall the solvents were evaporated
  4. dissolutionthe residue was redissolved in ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness by rotary evaporation
  8. customThe crude product was purified by silica gel flash chromatography
  9. washeluted with 20% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-fa44e9fe7fbf474f99b4ce12aa1a4d10
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238646B2

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