Reaktion #478479

Reaktionsgleichung

3-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile

N-((5-bromopyridin-3-yl)(cyclopropyl)methyl)ethanesulfonamide

Na2CO3

→

title compound

Ausbeute 56.0%

N-((5-(4-cyano-2-fluorophenyl)pyridin-3-yl)(cyclopropyl)methyl)ethanesulfonamide

Ausbeute 56.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige(General Suzuki reaction procedure 2)
2. 2
   SonstigeThe solvent was removed in vacuo
3. 3
   Sonstigethe residue was purified by flash column (EtOAc/Heptane, v/v, 0-50%)

Vorschrift

(General Suzuki reaction procedure 2) A mixture of 3-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile (333 mg, 1.35 mmol), N-((5-bromopyridin-3-yl)(cyclopropyl)methyl)ethanesulfonamide (430 mg, 1.35 mmol), PdCl2(PPh3)2 (77 mg, 0.10 mmol) and Na2CO3 (2M in water, 1.35 mL, 2.70 mmol) in DMF(6 mL) heated at 100° C. under N2 for 2 h. The solvent was removed in vacuo, and the residue was purified by flash column (EtOAc/Heptane, v/v, 0-50%) to give the title compound (270 mg, 56% yield); ESI-MS m/z: 360 [M+1]+. 1HNMR (MeOD, 400 MHz) δ 8.72 (1H, d, J=2.0 Hz), 8.71 (1H, d, J=2.0 Hz), 8.17 (1H, bs), 7.83-7.75 (3H, m), 3.95 (1H, d, J=8.8 Hz), 3.52 (3H, s), 3.05-2.92 (2H, m), 1.32-1.28 (1H, m), 1.30 (1H, t, J=7.2 Hz), 0.80-0.76 (1H, m), 0.67-0.61 (2H, m), 0.52-0.48 (1H, m). Enantiomers were separated by chiral HPLC (Chiralpak AS-H, EtOH/Heptane, v/v, 30/70) to the first peak (enantiomer 1, t=9.68 min), and the second peak (enantiomer 2, t=13.68 min).

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