Reacción #49276

Ecuación de reacción

3-amino-4-phenyl-6-bromophthalimide

5-(4-methylpiperazin-1-ylsulfonyl)-1H-indol-2-boronic acid

tri(o-tolyl)phosphine

triethylamine

1-(tert-butoxycarbonyl)-5-(4-methylpiperazin-1-ylsulfonyl)indol-2-boronic acid

→

3-amino-4-phenyl-6-[1-(tert-butoxycarbonyl)-5-(4-methylpiperazin-1-ylsulfonyl)indol-2-yl]phthalimide

Rendimiento 20.6%

Disolventes

acetonitrile

ethyl acetate methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrosynthesized in a similar manner to the literature [Bioorganic & Medicinal Chemistry Letters, 2004, vol. 14, p

Procedimiento

In a similar manner to Step 2 of Example 1, 3-amino-4-phenyl-6-bromophthalimide (70.0 mg, 0.221 mmol) was dissolved in acetonitrile (5.6 mL), and the solution was treated with a mixture (281 mg) of 1-(tert-butoxycarbonyl)-5-(4-methylpiperazin-1-ylsulfonyl)indol-2-boronic acid synthesized in a similar manner to the literature [Bioorganic & Medicinal Chemistry Letters, 2004, vol. 14, p. 351] and 5-(4-methylpiperazin-1-ylsulfonyl)-1H-indol-2-boronic acid, palladium acetate (4.0 mg, 0.018 mmol), tri(o-tolyl)phosphine (11 mg, 0.035 mmol) and triethylamine (0.308 mL, 2.21 mmol), followed by purification by preparative thin-layer chromatography (ethyl acetate/methanol=20/1) to obtain Compound 2 (21 mg, yield 19%) and 3-amino-4-phenyl-6-[1-(tert-butoxycarbonyl)-5-(4-methylpiperazin-1-ylsulfonyl)indol-2-yl]phthalimide (28 mg, yield 20%).

Fuente