Dichloromethane → HCID 72695031, compound

Participants

Reaction Conditions

Reaction Steps

The title compound was synthesized according to General Method C1 by utilizing N-(3-iodo-1H-indazol-5-yl)-2-(pyrrolidin-1-yl)-2-(thiophen-3-yl)acetamide (200 mg, 0.45 mmol), 6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxa-6-azaspiro[3.3]heptane (160 mg, 0.53 mmol), PdCl2dppf.DCM (36 mg, 0.044 mmol) and 2 M aq Na2CO3 (0.5 mL) in PhMe/EtOH (12 mL, 2:1 mixture). The reaction mixture was heated under microwave irradiation at 130° C. for 3 h. The reaction mixture was diluted with EtOAc (10 mL) and washed with H2O (5 mL), dried (MgSO4) and concentrated under vacuum to give a crude product. Purification by flash chromatography (Biotage Isolera, 50 g HP-SIL, 100% EtOAc then 0-10% DCM in MeOH) followed by trituration with MeOH gave the title compound as a light brown solid (46 mg, 18%). 1H NMR (400 MHz, CDCl3) δ ppm 9.21 (br. s., 1H), 8.38 (s, 1H), 7.83 (d, J=8.0 Hz, 2H), 7.48 (d, J=9.0 Hz, 1H), 7.42 (d, J=8.8 Hz, 1H), 7.29-7.36 (m, 2H), 7.15 (d, J=4.8 Hz, 1H), 6.58 (d, J=8.3 Hz, 2H), 4.87 (s, 4H), 4.15 (s, 1H), 4.09 (s, 4H), 2.61-2.75 (m, 2H), 2.47-2.60 (m, 2H), 1.76-1.92 (m, 4H); MS ESI 500.3 [M+H]+, calcd for [C28H29N5O2S+H]+ 500.2.

Provenance & Evidence