Pyridine → HCID 66799985, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 4-aminobenzoate (16 mg, 0.106 mmol), 5-isopropyl-3-methylbenzofuran-2-sulfonyl chloride (Intermediate 16) (40 mg, 0.147 mmol) and pyridine (20 μL, 0.25 mmol) in MeCN (600 μL) was stirred at 50° C. over night. The reaction mixture was diluted with MeOH/water and acidified by addition of TFA. The crude product was purified by reversed phase chromatography (ACE C8, 5 μm, 21×50 mm, flow 25 ml/min, 0.1% TFA in water/MeCN over 6 minutes). The title compound was obtained in 17% yield (6.7 mg). 1H NMR (500 MHz, MeOH-d4) δ ppm 1.28 (d, J=6.96 Hz, 6 H) 2.41 (s, 3 H) 3.02 (spt, J=6.96 Hz, 1 H) 3.85 (s, 3 H) 7.31-7.37 (m, 2 H) 7.37 (dd, J=8.67, 1.68 Hz, 1 H) 7.40 (dd, J=8.67, 0.75 Hz, 1 H) 7.46 (dt, J=1.68, 0.75 Hz, 1 H) 7.69-7.73 (m, 1 H) 7.82-7.84 (m, 1H). MS (ESI+) m/z 388 [M+H]+.

Provenance & Evidence