Dimethylformamide → HCID 178508590, compound

Participants

Reaction Conditions

Reaction Steps

To the DMF solution from the preparation of cis-7-(3-azetidin-1-ylmethylcyclobutyl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine were added 2-phenyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline (40 mg, 0.12 mmol), Na2CO3 (27 mg, 0.25 mmol), Pd(PPh3)4 (7 mg, 0.006 mmol), and water (0.6 mL). The solution was purged with nitrogen for 10 min and heated to 80° C. for 16 h. To the cooled reaction solution was added sat. Na2CO3 solution (10 mL), the mixture was extracted with EtOAc (3×20 mL), the combined organic layers were washed with water (3×15 mL) and brine, dried over MgSO4, filtered, and concentrated to give a brown oil. Purification by HPLC gave the title compound as brown oil. 1H NMR (CDCl3, 400 MHz): δ=2.06-2.26 (m, 5 H), 2.56-2.57 (d, 2 H, J=6.2), 2.71-2.77 (m, 2 H), 3.21-3.24 (m, 4 H), 5.17 (brs, 2 H), 5.19-5.26 (m, 1H), 7.31 (s, 1 H), 7.46-7.56 (m, 3 H), 7.69-7.71 (dd, 1 H, J=1.6 & 8.4 Hz), 7.90-7.94 (m, 2 H), 8.18-8.20 (m, 2 H), 8.26-8.29 (m, 2 H), 8.35 (s, 1 H). MS (ES+): 461.2 [MH+]. HPLC: tR=2.0 min (polar—5 min).

Provenance & Evidence