Reaktion #682919

Reaktionsgleichung

2,6-dichloro-3-iodopyridine

(E)-ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate

K2CO3

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title compound

(E)-ethyl 3-(2,6-dichloropyridin-3-yl)acrylate

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA steady stream of N2 was bubbled through the resultant mixture for 5 minutes
2. 2
   workup.ADDITIONthe mixture was diluted with EtOAc
3. 3
   Waschenthe organic layer washed successively with water (1×) and brine (1×)
4. 4
   TrocknenThe organic layer was dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

To a solution of 2,6-dichloro-3-iodopyridine (3.0 g, 10.95 mmol), (E)-ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate (2.476 g, 10.95 mmol), and Dichloro[1,1′-bis(di-tert-butylphosphino)ferrocene]palladium (II) (0.357 g, 0.548 mmol) in THF (81 mL) was added 1M (aq) K2CO3 (54.8 mL, 54.8 mmol). A steady stream of N2 was bubbled through the resultant mixture for 5 minutes. Stirring was continued at ambient temperature for 2 h then the mixture was diluted with EtOAc and the organic layer washed successively with water (1×) and brine (1×). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography using a gradient of 0-30% EtOAc/Hexanes as eluent to give the title compound as a tan solid. 1H NMR δ (ppm) (CHCl3-d): 7.95 (1H, d, J=16 Hz), 7.90 (1H, d, J=8.1 Hz), 7.35 (1H, d, J=8.1 Hz), 6.47 (1H, d, J=16 Hz), 4.32 (2H, q, J=7.15 Hz), 1.38 (3H, t, J=7.14 Hz). MS (M+H)+: 245.

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