Hydrochloric Acid → HCID 58423756, compound

Participants

Reaction Steps

A solution of t-butyl 6-bromo-2-phenyl-5′,6′-dihydrospiro[chroman-4,4′-[1,3]thiazine]-2′-ylcarbamate (41 mg, 0.084 mmol), 3-cyanophenylboronic acid (23.5 mg, 0.16 mmol), Cs2CO3 (78 mg, 0.24 mmol), and a catalytic amount of Pd(dppf)Cl2 in 1,4-dioxane (4 mL) and H2O (0.4 mL) is heated at 110° C. in microwave oven for 10 min. Then, 4 mL of 4 M HCl in 1,4-dioxane is added and stirred another 2 h at rt. Water (10 mL) is added and extracted with EA. The separated organic phase is washed with brine, and dried over Na2SO4, and filtered. The filtrate is concentrated to give a crude product which is purified through preparative HPLC to give 3-(2′-amino-2-phenyl-5′,6′-dihydrospiro[chroman-4,4′-[1,3]thiazine]-6-yl)benzonitrile. MS ESI+ve m/z 412 (M+H)+.

Provenance & Evidence