Triethylamine → HCID 18396233, compound

To a solution of 4-chloro-3-hydroxy-2-iodopyridine (1.04 g, 4.10 mmol) in DMF (10 mL) was added (Ph3P)2PdCl2 (0.140 g, 0.20 mmol), CuI (0.152 g, 0.80 mmol) and Et3N (0.496 g, 4.90 mmol). The mixture was stirred at room temperature for one hour. A solution of 1-Boc-2-(S)-ethynylpyrrolidine (0.80 g, 4.10 mmol), from step 1c above, in DMF (10 mL) was added and the mixture was heated at 60° C. for 16 hours. The reaction mixture was cooled to room temperature and poured into saturated NaHCO3 and washed with Et2O (4×100 mL). The combined organic extracts were washed with brine/H2O (1/1 400 mL), dried (MgSO4), and concentrated. The crude product was chromatographed (silica gel; CH2Cl2 /MeOH, 90:10) to afford the title compound as a brown oil (0.180 g, 14%): 1H NMR (CDCl3, 300 MHz) δ 1.40 (s, 9H), 1.95-2.10 (m, 4H), 3.10-3.25 (m, 2H), 4.90-5.10 (m, 1H), 6.65 (s, 1H), 7.10 (br s, 1H), 8.38 (br s, 1H); MS (DCI/NH3) m/z: 323 (M+H)+.

1. temperaturethe mixture was heated at 60° C. for 16 hours
2. temperatureThe reaction mixture was cooled to room temperature
3. washwashed with Et2O (4×100 mL)
4. washThe combined organic extracts were washed with brine/H2O (1/1 400 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. customThe crude product was chromatographed (silica gel; CH2Cl2 /MeOH, 90:10)

ORD record

ord-a0618f21e0e540c8812d0b7f44ffd79c

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06001849