Sodium Iodide → 1H-Indole, 4-iodo-6-(trifluoromethyl)-

To a suspension of 6-trifluoromethyl-1H-indol-4-ylamine (10.7 g, 53.4 mmol) in HCl (aq., 15%, 240 mL) was added a solution of sodium nitrite (5.52 g, 80.1 mmol) in H2O (10 mL) slowly at 0° C. The reaction mixture was stirred at RT for 1 h before a solution of sodium tetrafluoroborate (23.5 g, 0.214 mol) in H2O (30 mL) was added. After stirring for 15 min, the resulting precipitate was collected by filtration and washed with a sodium tetrafluoroborate solution (aq., sat) before dissolving in acetonitrile (100 mL). This solution was added slowly to a suspension of sodium iodide (24.0 g, 0.160 mol) in acetonitrile (100 mL) and the mixture stirred at RT for 16 h. The reaction mixture was concentrated to 30% of the volume and partioned between EtOAc and H2O. The organic layer was isolated then washed in succession with sodium thiosulfate, H2O and brine, dried over Na2SO4 and evaporated to dryness. The resulting brown oil was purified by column chromatography to give the title compound (9.77 g, 59%).

1. additionwas added
2. filtrationthe resulting precipitate was collected by filtration
3. washwashed with a sodium tetrafluoroborate solution (aq., sat)
4. dissolutionbefore dissolving in acetonitrile (100 mL)
5. stirringthe mixture stirred at RT for 16 h
6. concentrationThe reaction mixture was concentrated to 30% of the volume
7. customThe organic layer was isolated
8. washthen washed in succession with sodium thiosulfate, H2O and brine
9. dry with materialdried over Na2SO4
10. customevaporated to dryness
11. customThe resulting brown oil was purified by column chromatography

ORD record

ord-41082ff9f3e44847b922a9665758344f

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697693B2