Reacción #59681

Ecuación de reacción

4-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid

Intermediate 21

4-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid

3-methoxyaniline

di-isopropylethylamine

HATU

→

solid

Rendimiento 73.5%

N-(3-Methoxy-phenyl)-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide

Rendimiento 73.5%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was removed in vacuo
2. 2
   Otrothe residue partitioned between ethyl acetate (250 ml) and water (50 ml)
3. 3
   SecadoThe organic layer was dried over magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Otroremoved in vacuo
6. 6
   Otroto give the crude material
7. 7
   OtroThe product was purified
8. 8
   Lavadoeluting with 1:4 ethylacetate/cyclohexane

Procedimiento

4-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid (Intermediate 21) (2 g) was dissolved in dimethylformamide (20 ml). To this was added 3-methoxyaniline (0.985 g), di-isopropylethylamine (4 ml) and HATU (3.05 g). The mixture was stirred for 18 hours at room temperature. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (250 ml) and water (50 ml). The organic layer was dried over magnesium sulfate, filtered and removed in vacuo to give the crude material. The product was purified using silica Biotage cartridge (90 g) eluting with 1:4 ethylacetate/cyclohexane to give a white solid (2.06 g, 5.61 mmol).

Fuente