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HRID1485605

反应详情

EQUATION

反应方程式

HRID 1485605 的结构方程式

REACTANTS

反应物

3
结构：O=C([O-])[O-].[Na+].[Na+]
HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

结构：CC1(C)OB(c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)OC1(C)C
HCID10592495

2,2'-(1,4-Phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

C18H28B2O4

结构：C[Si](C)(C)CCOCn1c(O[C@@H]2CO[C@H]3[C@@H]2OC[C@H]3O)nc2cc(Cl)c(I)nc21
HCID123413447

未命名化合物

PRODUCTS

生成物

1
结构：CC1(C)OB(c2ccc(-c3nc4c(cc3Cl)nc(O[C@@H]3CO[C@H]5[C@@H]3OC[C@H]5O)n4COCC[Si](C)(C)C)cc2)OC1(C)C
HCID123678375

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

1
结构：C1COCCO1
溶剂HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度
70 °C

PROCEDURE

实验过程

A mixture of (3R,3aR,6R,6aR)-6-(6-chloro-5-iodo-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol (2.00 g), 1,4-benzenediboronic acid dipinacol ester (2.38 g), Na2CO3 (2 M aqueous solution, 5.42 mL), and 1,4-dioxane (15 mL) is purged for 5 minutes with argon. [1,1′-Bis(diphenylphosphino)-ferrocene]-dichloropalladium(II)-CH2Cl2-complex (PdCl2(dppf)×CH2Cl2) (206 mg) is added and the mixture is stirred over night at 70° C. The reaction mixture is partitioned between water and ethyl acetate. The organic phase is washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (dichloromethane/methanol 99:1→97:3) to give the title compound. LC (method 1): tR=1.27 min; Mass spectrum (ESI+): m/z=630 [M+H]+.

WORKUP

后处理

  1. customis purged for 5 minutes with argon
  2. addition[1,1′-Bis(diphenylphosphino)-ferrocene]-dichloropalladium(II)-CH2Cl2-complex (PdCl2(dppf)×CH2Cl2) (206 mg) is added
  3. customThe reaction mixture is partitioned between water and ethyl acetate
  4. washThe organic phase is washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on silica gel (dichloromethane/methanol 99:1→97:3)