Dichloromethane → HCID 58709962, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 4-[4-(3-iodo-4-methoxyphenylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylate (82.1 mg, 0.15 mmol), 3-thienylboronic acid (28.8 mg, 0.225 mmol) and potassium carbonate (41.5 mg, 0.3 mmol) in dioxane/water (4:1) (1.0 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II), complex with dichloromethane (1:1) (12 mg, 0.015 mmol). The resulting mixture was bubbled N2 for 5 min and then heated at reflux for 16 h. After cooled to rt, the solvents were removed under reduced pressure. The residue was dissolved in DMF (2 mL). The DMF solution was filtered and purified by HPLC to give the title compound. 1H-NMR (DMSO-d6, 400 MHz): δ=1.43 (s, 9H), 3.56 (m, 2H), 3.82 (s, 3H), 4.03 (m, 2H), 6.38 (s, br, 1H), 6.73 (s, 1H), 7.09 (d, J=9.2 Hz, 1H), 7.45 (dd, J=0.8, 5.2 Hz, 1H), 7.60 (dd, J=2.8, 4.8 Hz, 1H), 7.76 (m, 1H), 7.80 (dd, J=2.8, 8.8 Hz, 1H), 7.94 (d, J=2.8 Hz, 1H), 8.22 (s, 1H), 9.26 (s, 1H), 11.90 (s, 1H). MS (ES+): m/z 504.05 [MH+]. HPLC: tR=3.22 min (ZQ2000, polar—5 min).

Provenance & Evidence