Hydrochloric Acid → HCID 59582214, compound

Participants

Reaction Steps

To a dried flask under N2, were added 3,6-dibromo-9-(tetrahydro-2H-pyran-2-yl)-9H-carbazole (1) (37.5 g), aniline (25 mL), hexadecyltrimethylammonium bromide (430 mg), aqueous potassium hydroxide (68.6 g, 45% in water), toluene (1.2 L). The stirred mixture was purged with N2 for 15 min. Then to this mixture, were added Pd2 dba3 (4.12 g) and tri-tert-butylphosphine (2.97 g in anhydrous toluene). The reaction was heated to reflux overnight. The reaction was cooled down to room temperature, and anhydrous MgSO4 was added, and filtered through a layer of silica gel and celite. The solvent was removed and crude product was used for next reaction without purification. To a 2 L flask under N2, was added all the crude product of N3,N6-diphenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-carbazole-3,6-diamine (2), THF (1 L), and concentrated HCl (20 mL). The reaction mixture was stirred for 2 h. The THF (700 mL) was removed by evaporation, and then poured into ice water, filtered to obtain the solid crude product. The solid was stirring in ethyl acetate (500 mL) for 2 h, and filtration gave the final product (13.7 g) in 42% yield for two steps. 1H NMR was consistent with the compound.

Provenance & Evidence