Sodium Carbonate → HCID 72721745, compound

Participants

Reaction Conditions

Reaction Steps

The title compound was synthesized according to General Method C2 by utilizing (S)—N-(cyclopentyl(pyridin-2-yl)methyl)-3-iodo-1H-indazole-5-carboxamide (135 mg, 0.30 mmol), 6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxa-6-azaspiro[3.3]heptane (100 mg, 0.33 mmol), Pd(PPh3)4 (36 mg, 0.044 mmol) and 2 M aq Na2CO3 (0.3 mL) in PhMe/EtOH (14 mL, 1:1 mixture). The reaction mixture was heated under microwave irradiation at 130° C. for 3 h. The reaction mixture was diluted with EtOAc (20 mL) and washed with H2O (20 mL), dried (MgSO4) and concentrated under vacuum to give a crude product. Purification by flash chromatography (Biotage Isolera, 50 g HP-SIL, 60-100% EtOAc in hexanes then 0-20% DCM in MeOH) gave the product as a yellow solid. Further purification using reverse phase chromatography (Biotage Isolera, 50 g C18, 10-90% MeCN in H2O) followed by trituration with MeOH gave the title compound as a pale yellow solid (34 mg, 23%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.18 (s, 1H), 8.88 (d, J=8.3 Hz, 1H), 8.34-8.63 (m, 2H), 7.80-7.93 (m, 3H), 7.75 (t, J=6.9 Hz, 1H), 7.54 (d, J=8.5 Hz, 1H), 7.47 (d, J=8.0 Hz, 1H), 7.24 (t, J=5.3 Hz, 1H), 6.60 (d, J=8.5 Hz, 2H), 4.92 (t, J=9.0 Hz, 1H), 4.74 (s, 4H), 4.05 (s, 4H), 2.53-2.62 (m, 1H), 1.87 (s, 1H), 1.35-1.70 (m, 5H), 1.15-1.35 (m, 2H); MS ESI 494.4 [M+H]+, calcd for [C30H31N5O2+H]+ 494.3.

Provenance & Evidence