tert-Butyl 4-ethynylpiperidine-1-carboxylate → HCID 67347390, compound

Participants

Reaction Steps

Prepared from N-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide (Example 12, Step A, 350 mg, 0.592 mmol) and tert-butyl 4-ethynylpiperidine-1-carboxylate (186 mg, 0.888 mmol) using the procedure described for Example 6, Step B. The crude was purified by Biotage Flash 40M eluting with 20% EtOAc/hexanes (500 mL), 1:1 EtOAc/hexanes (1 L), followed by 2:1 EtOAc/hexanes (1.5 L). The product was isolated as a wax (293 mg, 68%). HPLC: 92% purity (254 nm); LRMS (APCI+): m/z 673, 573 (loss of BOC) (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 10.12 (s, 1H), 8.47 (d, J=6 Hz, 1H), 8.33 (s, 1H), 7.77 (m, 1H), 7.44 (m, 2H), 7.25 (m, 3H), 7.06 (t, J=9 Hz, 2H), 6.50 (d, J=6 Hz, 1H), 3.77 (m, 2H), 3.23 (m, 2H), 2.87 (m, 1H), 1.89 (m, 2H), 1.80 (m, 2H), 1.70 (m, 2H), 1.62 (m, 2H), 1.47 (s, 9H).

Provenance & Evidence