2-Propenoic acid, 3-(6-bromo-3-pyridinyl)-, methyl ester synthesis

Yield:918305-33-6 97%

Reaction Conditions:

in toluene; for 6 h;Heating / reflux;

Steps:

15.1

Example 15: 3-(6-Bromo-pyridin-3-yl)-N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-acrylamide [Show Image] Step 1: 3-(6-Bromo-pyridin-3-yl)-acrylic acid methyl ester To 6-Bromo-pyridine-3-carboxaldehyde (300 mg, 1.61 mmol) in toluene was added Methyl(Triphenylphosphoranylidene)acetate (647 mg, 1.94 mmol) and the solution was refluxed for 6 hrs. The reaction mixture was diluted with EtOAc and then washed three times with H₂O, brine, dried. Na₂SO₄, filtered and concentrated under reduced pressure. The obtained residue was column-chromatographed to yield 3-(6-Bromo-pyridin-3-yl)-acrylic acid methyl ester (380 mg, 97 %). ¹H NMR (300 MHz, CDCl₃): δ 8.47 (d, 1H, J=2.4 Hz), 7.68 (dd, 1H, J=8.4, 2.4 Hz), 7.60 (d, 1H, J=15.9 Hz), 7.51 (d, 1H, J=8.4 Hz), 6.49 (d, 1H, J=15.9 Hz), 3.81 (s, 3H).

References:

EP1882687,2008,A1 Location in patent:Page/Page column 26-27