Reaktion #159834

Reaktionsgleichung

Methanesulfonyl chloride

(E)-2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-amine

→

product

Ausbeute 32.0%

(E)-N-(2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-yl)methanesulfonamide

Ausbeute 32.0%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter evaporated to dryness
2. 2
   Sonstigethe residue was purified by silica gel chromatography
3. 3
   Wascheneluting with PE/EtOAc (1:2 v/v)

Vorschrift

Methanesulfonyl chloride (0.048 mL, 0.31 mmol) was added dropwise into the solution of (E)-2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-amine (111 mg, 0.28 mmol) in dry pyridine (7 mL) on an ice bath. After warming up to room temperature the mixture was stirred overnight. After evaporated to dryness, the residue was purified by silica gel chromatography, eluting with PE/EtOAc (1:2 v/v) to afford pure product as a white solid (42 mg, 32%) 1H-NMR (Acetone-do): δ 2.98 (s, 3H, CH3), 3.90 (s, 3H, OCH3), 3.93 (s, 6H, 2×OCH3), 3.97 (s, 3H, OCH3), 4.38 (s, 2H, CH2), 6.31 (s, 2H, Ph-H), 7.19 (d, 1H, J=15.6 Hz, CH), 7.71 (d, 1H, J=15.6 Hz, CH), 7.85 (d, 1H, J=2.0 Hz, Py-H), 7.97 (d, 1H, J=2.0 Hz, Py-H); 13C-NMR (Acetone-d6): δ 38.78, 53.30, 55.08, 55.53, 57.36, 90.67, 103.24, 119.44, 121.70, 123.17, 130.21, 134.70, 143.67, 154.11, 161.54, 164.28; HR-MS (ESI+) m/z 473.1115 [M+H]+ C19H24N2O832 requires 472.0974.

Quelle