반응 #478483

반응 방정식

2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile

N-((5-bromopyridin-3-yl)(cyclopropyl)methyl)propane-2-sulfonamide

Na2CO3

→

title compound

수율 67.0%

N-((5-(3-chloro-4-cyanophenyl)pyridin-3-yl)(cyclopropyl)methyl)-propane-2-sulfonamide

수율 67.0%

용매

DMF

반응 조건

후처리

1. 1
   농축After concentration
2. 2
   workup.DISSOLUTIONthe resulting residue was dissolved in DCM
3. 3
   여과filtered
4. 4
   농축The filtrates were concentrated
5. 5
   기타purified by flash column (EtOAc/Heptane, v/v, 0-40%)

실험 절차

A mixture of 2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile (198 mg, 0.75 mmol), N-((5-bromopyridin-3-yl)(cyclopropyl)methyl)propane-2-sulfonamide (250 mg, 0.75 mmol), PdCl2(PPh3)2 (43 mg, 0.06 mmol) and Na2CO3 (2 M in water, 0.94 mL, 1.88 mmol) in DMF(6 mL) was heated at 100° C. for 2 h. After concentration, the resulting residue was dissolved in DCM and filtered. The filtrates were concentrated and purified by flash column (EtOAc/Heptane, v/v, 0-40%) to give the title compound (195 mg, 67%); ESI-MS m/z: 390 [M+1]+; 1H-NMR (MeOD, 400 MHz) δ 8.84 (1H, s), 8.71 (1H, s), 8.25 (1H, s), 8.05 (1H, bs), 7.98 (1H, d, J=8.0 Hz), 7.86 (1H, d, J=8.0 Hz), 3.97 (1H, d, J=9.2 Hz), 3.16-3.09 (1H, m), 1.37-1.33 (1H, m), 1.36 (3H, d, J=7.2 Hz), 1.29 (3H, d, J=7.2 Hz), 0.81-0.76 (1H, m), 0.66-0.63 (2H, m), 0.53-0.48 (1H, m); Enantiomers were separated by chiral HPLC (ChiralPak IA-H, EtOH/Heptane, v/v, 60/40) to give the first peak (enantiomer 1, t=10.11 min) and the second peak (enantiomer 2, t=12.95 min).

출처