Water → tert-Butyl N-[(1S)-1-[4-(2-aminophenyl)pyridin-2-yl]but-3-en-1-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

45C (2 g, 7.07 mmol) and (2-aminophenyl)boronic acid (1.065 g, 7.78 mmol) in DMSO (35.4 ml) and H2O (0.637 ml, 35.4 mmol) was de-gassed for 30 min. Then, Phosphoric acid, potassium salt (3.00 g, 14.15 mmol) and 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium(ii) dichloromethane complex (0.518 g, 0.707 mmol) were added. The dark red reaction mixture was sealed and heated at 90° C. overnight. The reaction mixture was diluted with EtOAc/Ether and washed with water and brine. The organic layer was dried over MgSO4. Filtered and concentrated to give the crude product as a black oil. The residue was purified by silica gel chromatography to give the desired product (2.0 g, 83%) as a light brownish foam. 1H NMR (400 MHz, CHLOROFORM-d) δ 8.61 (d, J=4.8 Hz, 1H), 7.37-7.28 (m, 2H), 7.27-7.16 (m, 2H), 7.12 (d, J=7.7 Hz, 1H), 6.85 (t, J=7.5 Hz, 1H), 6.77 (d, J=7.9 Hz, 1H), 5.79-5.58 (m, 2H), 5.12-4.97 (m, 2H), 4.90-4.80 (m, 1H), 3.80 (br. s., 2H), 2.62 (t, J=6.6 Hz, 2H), 1.44 (s, 9H). MS (ESI) m/z: 340.1 (M+H)+.

Provenance & Evidence