1,2-Dichloroethane → HCID 89962092, compound

Participants

Reaction Steps

EDC (310 mg, 1.6 mmol) was added to DMF (4 mL) solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (200 mg, 0.81 mmol), 2-methoxy-N-methylethanamine (144 mg, 1.6 mmol), TEA (0.23 mL, 1.6 mmol) and HOBT hydrate (247 mg, 1.60 mmol). After 3 days at room temperature, the reaction mixture was diluted in water (15 mL), extracted with DCM (3×10 mL), the combined organic portions dried over Na2SO4, filtered, concentrated under reduced pressure and purified by reverse phase HPLC (Phenomemenx Luna AXIA 5 micron C18, 21.2×100, UV at 220 nm, 10 to 70% B over 30 minutes with 10 minute hold time, solvent A: 90% water/ACNl/0.1% TFA, solvent B:90% ACN/water/0.1% TFA, Flow rate 20 mL/min; detector at 254) to isolate Compound B172a (47 mg, 18% yield) as a clear oil. HPLC: RT=0.96 min (LCMS Method M). MS (ES): m/z=319.7 [M+H]+. 1H NMR (500 MHz, CHLOROFORM-d) δ 9.45-8.71 (m, 1H), 7.85 (d, J=7.2 Hz, 2H), 7.40 (d, J=8.0 Hz, 2H), 3.89-3.64 (m, 2H), 3.42 (d, J=12.1 Hz, 3H), 3.34-3.12 (m, 3H), 3.04 (s, 2H), 1.36 (s, 12H).

Provenance & Evidence