Tert-Butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate synthesis

Yield:400801-82-3 73%

Reaction Conditions:

with sodium methylate in methanol; for 2.5 h;Heating / reflux;

Steps:

3.1

Example 3 Preparation of the compound I-13 [Show Image] Step 1 To a solution of the compound(6)(5.0 g, 42.3 mmol) in methanol(50 mL) were added 1-(t-butoxycarbonyl)-4-piperidone(16.9 g, 84.6 mmol) and a 28% methanol solution of sodium methoxide(50 mL, 0.25 mmol) and the solution was heated under reflux for 2.5 hours. The reaction solution was poured into 100 mL of ice water, extracted with ethyl acetate and the organic layer was washed with water, dried and concentrated. The resulting residue was crystallized from hexane-ethyl acetate to give the compound(7)(9.23 g, 73% yield). ¹H-NMR(CDCl₃) δ ppm: 1.51 (s, 9H), 2.57 (s, 2H), 3.61-3.71 (m, 2H), 4.14-4.24 (m, 2H), 6.15 (s, 1H), 7.13-7.18 (m, 1H), 7.40 (s, 1H), 8.22 (d, 1H, J = 9.3 Hz), 8.32-8.34 (m, 1H), 10.2 (br, 1H).

References:

EP1911759,2008,A1 Location in patent:Page/Page column 37-39