Toluene → Tert-butyl 5-(3-fluorophenyl)picolinate

HRID 711242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 711242
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[N:6][CH:7]=1.[F:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>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.C(O)C>[F:15][C:16]1[CH:21]=[C:20]([C:2]2[CH:3]=[CH:4][C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[N:6][CH:7]=2)[CH:19]=[CH:18][CH:17]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 24997839tert-Butyl 5-bromopyridine-2-carboxylate

Produkt 1

HCID 67208627Tert-butyl 5-(3-fluorophenyl)picolinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a reaction flask was added tert-butyl 5-bromopicolinate 33-4 (516 mg, 2.00 mmol), 3-fluorophenylboronic acid 6-6 (280 mg, 2.00 mmol), Pd(PPh3)4 (140 mg, 0.20 mmol), toluene (10 mL), ethanol (2 mL) and 2M Na2CO3 (3 mL). The reaction mixture was bubbled with nitrogen for 2 minutes and stirred at 90° C. for 10 hours with the flask sealed. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (100 mL) and washed with saturated NaHCO3 aqueous solution, H2O and brine. The organic phase was dried over Na2SO4 and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, and eluted with 30% hexanes in ethyl acetate to give tert-butyl 5-(3-fluorophenyl)picolinate 33-5 as a white solid. MS m/z 274.1 (M+1).

Aufarbeitung

  1. customThe reaction mixture was bubbled with nitrogen for 2 minutes
  2. customsealed
  3. temperatureAfter cooling to room temperature
  4. additionthe reaction mixture was diluted with ethyl acetate (100 mL)
  5. washwashed with saturated NaHCO3 aqueous solution, H2O and brine
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated to dryness by rotary evaporation
  8. customThe crude product was purified by silica gel flash chromatography
  9. washeluted with 30% hexanes in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b7575e6a2afd41e2b9fe986ac056e729
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181235B2

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