반응 #84096

ord-22fc8e2e1637487cbda154f2dea039f9

반응 방정식

COc1ccc2nc(-c3ccc(-c4nnn[nH]4)cc3)c(C)cc2c1
2-chloro-6-methoxyquinoline
COc1ccc2nc(-c3ccc(-c4nnn[nH]4)cc3)c(C)cc2c1
2-(4-(1H-tetrazol-5-yl)phenyl)-6-methoxy-3-methylquinoline
COc1ccc2nc(-c3ccc(-c4nnn[nH]4)cc3)c(C)cc2c1
Intermediate 1
COc1ccc2nc(-c3ccc(-c4nnn[nH]4)cc3)c(C)cc2c1
2-(4-(1H-tetrazol-5-yl)phenyl)-6-methoxy-3-methylquinoline
COC(=O)c1ccc(B(O)O)cc1
4-(methoxycarbonyl) phenylboronic acid
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
COC(=O)c1ccc(-c2ccc3cc(OC)ccc3n2)cc1
product
수율 40.9%
COC(=O)c1ccc(-c2ccc3cc(OC)ccc3n2)cc1
methyl 4-(6-methoxyquinolin-2-yl)benzoate
수율 40.9%

반응 조건

온도
120°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    여과The precipitates were filtered
  2. 2
    세척washed with EA (10 mL), acetone (10 mL) and water (10 mL) separately
  3. 3
    기타dried

실험 절차

A mixture of 2-chloro-6-methoxyquinoline (Intermediate 1, 200 mg, 1.0 mmol), 4-(methoxycarbonyl) phenylboronic acid (205 mg, 1.1 mmol), Pd(dppf)Cl2 (366 mg, 0.5 mmol) and sodium carbonate (212 mg, 2.0 mmol) in 1,4-dioxane/water (3 mL/0.6 mL) was heated to 120° C. by microwave for 1 h. The precipitates were filtered; washed with EA (10 mL), acetone (10 mL) and water (10 mL) separately; dried to afford product (120 mg, 40.9%).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US09433618B2uspto-grants-2016_09