tert-butyl 4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)piperidine-1-carboxylate

Participants

Reaction Steps

A round-bottomed flask was charged with tert-butyl 4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl) -5,6-dihydropyridine-1(2H)-carboxylate (Example 149, Step A, 146.3 mg, 0.3314 mmol), palladium on carbon (117.7 mg, 0.099 mmol, 10%) and MeOH (10 mL). The air was exchanged with nitrogen three times and then was exchanged with hydrogen another three times. Then the reaction mixture was stirred under hydrogen at room temperature until the starting material had been consumed (2 hours). The mixture was filtered to remove the palladium on carbon and then the solvent was removed under reduced pressure to afford crude product. The crude product was purified by silica gel chromatography (dichloromethane/7 M NH3 in MeOH from 100/1 to 10/1, v/v) to afford product (144.5 mg, 98.3%). LRMS (APCI pos): >95% purity, 254 nm, m/e 444 (M+1). 1H NMR (400 MHz, CD3Cl) δ 8.41 (d, 1H), 7.27 (m, 1H), 7.02 (t, 1H), 6.54 (dd, 1H), 6.46 (m, 2H), 4.24 (m, 2H), 3.84 (br s, 2H), 3.07 (m, 1H), 2.88 (m, 2H), 2.09 (m, 2H), 1.74 (m, 2H), 1.49 (s, 9H).

Provenance & Evidence