2-Bromo-3-pyridinol → 6-Bromo-3-methoxy-2-nitropyridine

Participants

Reaction Steps

Starting material -2-amino-6-bromo-5-methoxybromo-pyridine, was prepared in following manner: 2-bromopyridin-3-ol (Aldrich) was converted to 2-bromo-3-methoxy-6-nitropyridine as described in J. Med. Chem. 1981, 24, 39-42. Hydrogenation of 2-bromo-6-nitro-5-methoxypyridine in ethanol (Pt on C, 1 atm) gave the starting material as a reddish oil. This product was then condensed with cis/trans mixture of 2-(2-chloro-3-ethoxy-6-fluorophenyl)cyclopropylisocyanates, described in Example 53, in a manner analogous to the method in Example 7 to provide cis/trans (50:50) mixture of N-2-(2-Chloro-3-ethoxy-6-fluorophenyl)-cyclopropyl-N'-(6-bromo-5-hydroxypyrid-2-yl)-ureas. 1H NMR (250 MHz, CDCl3) δ 7.62-7.43 (m, 1H), 7.29-7.12 (m, 1H), 6.91-6.67 (m, 2H), 4.10-3.94 (m, 2H), 3.90 and 3.84 (2 s, 3H),3.38-3.02 (m, 1H) 2.18-2.00 (m, 1H), 1.55-1.30 H (m, 5H), 1.43 (t, 3H), 0.92-0.80 (m, 2H).

Provenance & Evidence