Реакция #59681

Уравнение реакции

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

Выход 73.5%

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

Выход 73.5%

Растворители

dimethylformamide

Условия реакции

Обработка

1. 1
   ДругоеThe solvent was removed in vacuo
2. 2
   Другоеthe residue partitioned between ethyl acetate (250 ml) and water (50 ml)
3. 3
   СушкаThe organic layer was dried over magnesium sulfate
4. 4
   Фильтрацияfiltered
5. 5
   Другоеremoved in vacuo
6. 6
   Другоеto give the crude material
7. 7
   ДругоеThe product was purified
8. 8
   Промывкаeluting with 1:4 ethylacetate/cyclohexane

Методика

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).

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