Reacción #620443

Ecuación de reacción

mixture

methyl 4-bromo-3-formyl-1-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate

o-tolylboronic acid

tri-t-butyl-phosphonium tetrafluoroborate

CsF

→

methyl 3-formyl-1-(3-(naphthalen-1-yloxy)propyl)-4-o-tolyl-1H-indole-2-carboxylate

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was purged with Argon
2. 2
   workup.ADDITIONThe mixture was diluted with ethyl acetate (200 mL)
3. 3
   Lavadowashed with water and brine
4. 4
   Secadodried over Na2SO4
5. 5
   FiltraciónAfter filtration, concentration of the solvent and column purification (5% ethyl acetate in hexane)
6. 6
   Otroprovided EXAMPLE 107C

Procedimiento

To a mixture of EXAMPLE 107B (0.5 g) and o-tolylboronic acid (175 mg) in tetrahydrofuran (5 ml) was added tris(dibenzylideneacetone)dipalladium(0) (25 mg), tri-t-butyl-phosphonium tetrafluoroborate (16 mg) and CsF (489 mg). The mixture was purged with Argon and stirred at room temperature for 24 hours. The mixture was diluted with ethyl acetate (200 mL) and washed with water and brine and dried over Na2SO4. After filtration, concentration of the solvent and column purification (5% ethyl acetate in hexane) provided EXAMPLE 107C.

Fuente