反応 #59681

反応方程式

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

収率 73.5%

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

収率 73.5%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   その他The solvent was removed in vacuo
2. 2
   その他the residue partitioned between ethyl acetate (250 ml) and water (50 ml)
3. 3
   乾燥The organic layer was dried over magnesium sulfate
4. 4
   ろ過filtered
5. 5
   その他removed in vacuo
6. 6
   その他to give the crude material
7. 7
   その他The product was purified
8. 8
   洗浄eluting with 1:4 ethylacetate/cyclohexane

実験手順

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).

出典