Nitrogen → HCID 178472381, compound

Participants

Reaction Conditions

Reaction Steps

A solution of cis-4-(4-amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-cyclohexanecarboxylic acid ethyl ester (16.2 mg 0.0391 mmol), 2-phenyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline (15.6 mg, 1.2 eq.), Pd(PPh3)4 (2.7 mg, 0.06 eq.) and Na2CO3 (10.4 mg, 2.5 eq.) in DMF (2.5 mL)/H2O (0.5 mL) was flushed with N2 for 30 min at rt and heated at 80° C. for 16 h under nitrogen. After that time, the reaction mixture was treated with H2O and extracted with EtOAc (3×10 mL). The combined extracts were washed with H2O (2×5 mL) and brine (5 mL), and dried over MgSO4. The drying agent was filtered off, the filtrate was concentrated in vacuo, and the crude yellow oil was purified by HPLC to obtain the title compound as yellow oil. 1H NMR (CDCl3, 400 MHz): δ=1.29-1.36 (t, 3 H, J=7.2 Hz), 1.74-2.09 (m, 6 H), 2.34-2.41 (m, 2 H), 2.75 (m, 1 H), 4.19-4.25 (q, 2 H, J=7.2 Hz), 4.77-4.85 (m, 1 H), 5.22 (brs, 2 H), 7.22 (s, 1 H), 7.46-7.57 (m, 3 H), 7.68-7.70 (dd, 1 H, J=1.6 & 8.0 Hz), 7.89-7.93 (m, 2 H), 8.18-8.20 (dd, 2 H, J=0.8 & 8.0 Hz), 8.25-8.27 (m, 2 H), 8.37 (s, 1 H). MS (ES+): 492.1 [MH+]. HPLC: tR=3.1 min (polar—5 min).

Provenance & Evidence