1-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid → 2-(3-Sulfamoyl-phenyl)-pyrrole-1-carboxylic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

A mixture of 3A, 3-bromobenzene sulfonamide (0.1 g, 0.4 mmol) in DME (6 mL) and 2.0 M Na2CO3 (0.8 mL) was degassed by bubbling argon for 5 min. To this solution, Pd(PPh3)4 (28 mg, 0.025 mmol) was added. The mixture was heated at 92° C. for 3 h. After cooling to rt, it was extracted with EtOAc, and dried over Na2SO4. The crude product was purified by silica gel chromatography (hexanes/EtOAc=3/1) to give 3B (293 mg, 90% yield) as a semi-solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.37 (s, 9H) 4.88 (s, 2H) 6.23 (m, 1H) 7.36 (m, 1H) 7.47 (t, J=7.69 Hz, 1H) 7.55 (m, 1H) 7.83 (d, J=8.35 Hz, 1H) 7.90 (s, 1H).

Provenance & Evidence