2-broMo-6-(Methylsulfonyl)pyridine synthesis

Yield:98626-92-7 69%

Reaction Conditions:

with 3-chloro-benzenecarboperoxoic acid in dichloromethane at 20; for 2 h;

Steps:

67.A

Example 67.; Preparation of 8-(1-ethyl-propyl)-3-[5-(6-methanesulfonyl-pyridin-1-yl)-3-methyl- thiophen-2-yl]-2,6-dimethyl-imidazo[1,2-b]pyridazine.; A. 2-Bromo-6-methanesulfonyl-pyridine.; To a solution of 2-bromo-6-methylsulfanyl-pyridine (Testaferri et. el Tetrahedron, 1985, 41, 1373) (2.15 g, 10.53 mmol) and CH₂Cl₂ (30 mL) is added 56-87% mCPBA (12 g, 42.15 mmol). The solution is cooled with ice to ambient temperature and the solution is stirred for 2 hour, washed with sat. Na₂S₂O₃ (15 mL), sat. NaHCO₃ (2 X 15 mL) dried over MgSO₄, filtered and concentrated. The residue is purified by recrystalization from EtOAc /hexane furnish the title compound (1.71 g, 7.24 mmol, 69%). ¹H NMR (CDCl₃), δ 3.26 (s, 3H), 7.73 (dd, J = 8.0, 0.9 Hz, 1H), 7.82 (dd, J = 8.0, 7.5 Hz, 1H), 8.05 (dd, J = 7.5, 0.9 Hz, 1H). LC/MS (m/z): calcd. for C₆H₆BrNO₂S (M+H)⁺: 235.9; found: 235.9.

References:

WO2006/102194,2006,A1 Location in patent:Page/Page column 70