Preparation method of benzoheterocyclic boric acid
A technology of benzoheterocyclic boronic acid and benzo, applied in the field of organic synthesis, can solve the problems of limited production, low reaction yield, low yield and the like, and achieves the effects of being beneficial to industrialized production, fast reaction rate and high yield
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Embodiment 1
[0051] This example prepares 1,4-benzodioxane-6-boronic acid through the following steps, and the specific reaction formula is as follows:
[0052]
[0053] (1) Dissolve 0.01mol of 6-bromo-1,4-benzodioxane in 5mL of DMSO to obtain solution A, and dissolve 0.016mol of di(neopentyl glycol) diboron in 4mL of In DMSO, to obtain B solution, 0.005mol of PbCl 2 (dppf) and 0.02mol potassium acetate are immobilized on the channel of the continuous flow reactor, and the A solution and the B solution are continuously fed and reacted at 90° C. for 15 minutes, and the reaction is terminated after flowing out of the reaction tube to obtain an intermediate;
[0054] (2) The intermediate obtained in step (1) was hydrolyzed with hydrochloric acid at 30° C. for 3 h, and then extracted and purified to obtain 1,4-benzodioxane-6-boronic acid with a yield of 92.1%.
[0055] 1 H NMR (400MHz, DMSO-d 6 ) δ 7.38-7.26 (m, 3H), 4.72 (s, 2H), 4.27 (d, J=4.0Hz, 4H).
Embodiment 2
[0057] This embodiment prepares 1-methylindole-5-boronic acid through the following steps, and the specific reaction formula is as follows:
[0058]
[0059] (1) Dissolve 0.01mol of 5-bromo-1-methylindole in 10mL of DMF to obtain solution A, and dissolve 0.02mol of bis(pinacolate) diboron in 15mL of DMF to obtain solution B , 0.5 mmol of palladium acetate and 0.01 mol of potassium acetate are immobilized on the channel of a continuous flow reactor, and the A solution and the B solution are continuously fed and reacted at 50 ° C for 90 minutes, and the reaction is terminated after flowing out of the reaction tube to obtain an intermediate;
[0060] (2) The intermediate obtained in step (1) was hydrolyzed with hydrochloric acid at 25° C. for 6 h, and then extracted and purified to obtain 1-methylindole-5-boronic acid with a yield of 87.3%.
[0061] 1 H NMR (400MHz, DMSO-d 6 )δ7.55-7.08 (m, 3H), 6.97 (s, 1H), 6.38 (s, 1H), 4.79 (s, 2H), 3.72 (s, 3H).
Embodiment 3
[0063] The present embodiment prepares 6-quinoline boronic acid through the following steps, and the specific reaction formula is as follows:
[0064]
[0065] (1) 0.01mol of 6-bromoquinoline was dissolved in 4.16mL of DMSO to obtain A solution, 0.011mol of bis(pinacolate) diboron was dissolved in 8.4mL of DMSO to obtain B solution, and 0.05 One mmol of palladium acetate and 0.05 mol of cesium carbonate are immobilized on the channel of the continuous flow reactor, and the A solution and the B solution are continuously fed and reacted at 150° C. for 6 minutes, and the reaction is terminated after flowing out of the reaction tube to obtain an intermediate;
[0066] (2) After hydrolyzing the intermediate obtained in step (1) with hydrochloric acid for 0.5 h at 50° C., 6-quinolineboronic acid was obtained through extraction and purification with a yield of 86.4%.
[0067] 1 H NMR (400MHz, DMSO-d 6 )δ8.90-8.09 (m, 6H), 4.75 (s, 2H).
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