Dichloromethane → Tert-butyl 3-((4-(5-amino-6-(5-phenyl-1,3,4-thiadiazol-2-yl)pyrazin-2-yl)phenyl)sulfonyl)piperidine-1-carboxylate

Participants

Reaction Steps

A mixture of tert-butyl 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]sulfonylpiperidine-1-carboxylate (162.0 mg, 0.3590 mmol), 5-bromo-3-(5-phenyl-1,3,4-thiadiazol-2-yl)pyrazin-2-amine (100 mg, 0.2992 mmol), Pd(dppf)Cl2.DCM (24.43 mg, 0.02992 mmol) and Na2CO3 (448.8 μL of 2 M, 0.8976 mmol) in dioxane (2 mL) was irradiated by microwave at 100° C. for 30 minutes. The mixture was diluted with water and the aqueous layer was extracted with EtOAc (×2). The combined organic extracts were washed with brine (×1), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion, 24 g column, eluting with 0 to 50% EtOAc/Petroleum Ether, loaded in DCM) to give the sub-title product as a yellow solid (173 mg, 100% Yield). 1H NMR (400.0 MHz, DMSO-d6) δ 9.04 (s, 1H), 8.36 (d, 2H), 8.16 (br s, 2H), 8.13 (dd, 2H), 8.01 (d, 2H), 7.64-7.61 (m, 3H), 4.10-3.95 (m, 1H), 3.76 (br d, 1H), 2.99-2.74 (m, 2H), 2.12-2.02 (m, 1H), 1.75-1.59 (m, 2H) and 1.35-1.32 (m, 11H) ppm; LC/MS m/z 579.2 [M+1]+.

Provenance & Evidence