(2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazol-6-yl)(pyridine-2-yl)methanone → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-(pyridin-2-yl)vinyl)benzo[d]thiazole

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (2.5 M in hexanes, 1.80 mL, 4.50 mmol) was added to a suspension of methyltriphenylphosphonium bromide (1.78 g, 5.00 mmol) in THF (10 mL) at −78° C. and the mixture was warmed to 0° C. over 30 min. The suspension (1 mL, about 3 equiv Wittig reagent) was added to a suspension of (2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-benzo[d]thiazol-6-yl)(pyridine-2-yl)methanone (0.09 g, 0.21 mmol) in THF (1 mL) and the mixture was stirred for 16 h at RT. The solvent was remove under vacuum and the resulting oil was purified by silica gel chromatography to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-(1-(pyridin-2-yl)vinyl)benzo[d]thiazole as a white solid. MS (ESI) m/z: Calculated: 418.1; Observed: 419.1 (M++1).

Provenance & Evidence