反应详情

A solution of 6-fluoro-3-iodo-1H-indole-5-carboxylic acid (650 mg, 2.13 mmol) in DMF (5 mL) at 0° C. was treated with NaH (60% dispersion in mineral oil, 0.213 g, 5.33 mmol). After 30 minutes at 0° C., TsCl (0.447 g, 2.34 mmol) was added in 1 portion and the reaction mixture was warmed slowly in the ice bath (reached ca. 10° C.). After 1.5 h, the reaction mixture was poured onto ice, and the pH adjusted to pH 5 with 2 N HCl causing precipitation of the product. It was then collected by filtration, washing with water on a sintered glass frit, transferred to a flask and dried on a lyopholizer for 5 h affording 6-fluoro-3-iodo-1-tosyl-1H-indole-5-carboxylic acid (858 mg, 1.87 mmol, 88% yield) as an off-white amorphous solid. MS (ESI, pos. ion) m/z: 459.8 (M+H)+. The crude material was used in the subsequent step without further purification.

1. waitAfter 1.5 h
2. additionthe reaction mixture was poured onto ice
3. customthe pH adjusted to pH 5 with 2 N HCl causing precipitation of the product
4. filtrationIt was then collected by filtration
5. washwashing with water on a sintered glass frit
6. customtransferred to a flask
7. customdried on a lyopholizer for 5 h