Sodium Carbonate → 4-(1-Phenylazulene-2-yl)phenylsulfonamide

Participants

Reaction Steps

Methyl 2-(4-t -butylaminosulfonylphenyl) azulene-1-carboxylate: To a solution of methyl 2-chloroazulene-1-carboxylate (0.50 g) in toluene (20.0 ml) was added 4-t-butylaminosulfonyl-phenylboronic acid (0.87 g), tetrakis(triphenylphosphine)palladium (0) (0.12 g), and 2M aqueous Na2CO3 (4.5 ml), and the reaction mixture was heated under reflux for 16 hr. The mixture was poured into ice-water, followed by extracted with EtOAc. The combined EtOAc extracts were washed with water and brine, dried over Na2SO4, and concentrated. The crude product was purified by SiO2 column chromatography (CHCl3 /EtOAc, 100:1) to give the title compound (1.13 g) as violet crystals; mp 169°-170° C.

Provenance & Evidence