Reaction #59681

Reaction equation

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

Yield 73.5%

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

Yield 73.5%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   OtherThe solvent was removed in vacuo
2. 2
   Otherthe residue partitioned between ethyl acetate (250 ml) and water (50 ml)
3. 3
   DryingThe organic layer was dried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Otherremoved in vacuo
6. 6
   Otherto give the crude material
7. 7
   OtherThe product was purified
8. 8
   Washeluting with 1:4 ethylacetate/cyclohexane

Procedure

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).

Source