Reaktion #59681

Reaktionsgleichung

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

Ausbeute 73.5%

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

Ausbeute 73.5%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed in vacuo
2. 2
   Sonstigethe residue partitioned between ethyl acetate (250 ml) and water (50 ml)
3. 3
   TrocknenThe organic layer was dried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Sonstigeremoved in vacuo
6. 6
   Sonstigeto give the crude material
7. 7
   SonstigeThe product was purified
8. 8
   Wascheneluting with 1:4 ethylacetate/cyclohexane

Vorschrift

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).

Quelle