乙酸钾 → 6-oxo-1-(2-trimethylsilanylethoxymethyl)-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-1,6-dihydropyridazine-3-boronic acid

HRID 12286

反应方程式

HRID 12286 反应方程式
Cl[C:2]1[CH:3]=[C:4]([C:17]2[N:21]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:20]3[CH:30]=[CH:31][CH:32]=[CH:33][C:19]=3[N:18]=2)[C:5](=[O:16])[N:6]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[N:7]=1.[B:34]1(B2OC(C)(C)C(C)(C)O2)[O:38]C(C)(C)C(C)(C)[O:35]1.C([O-])(=O)C.[K+]>CS(C)=O>[O:16]=[C:5]1[N:6]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[N:7]=[C:2]([B:34]([OH:38])[OH:35])[CH:3]=[C:4]1[C:17]1[N:21]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:20]2[CH:30]=[CH:31][CH:32]=[CH:33][C:19]=2[N:18]=1

参与物

5

反应物 3

HCID 517044乙酸钾HCID 2733548联硼酸频那醇酯HCID 686802706-chloro-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one

产物 1

HCID 686797026-oxo-1-(2-trimethylsilanylethoxymethyl)-5-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-1,6-dihydropyridazine-3-boronic acid

试剂、催化剂与溶剂 1

HCID 679二甲基亚砜溶剂

反应条件

温度
95 °C

实验过程

4 g of 6-chloro-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanylethoxy-methyl) -1H-benzimidazol-2-yl]-2H-pyridazin-3-one (example 46), 4.1 g of bis(pinacolato)diboron, 0.19 g of (1,1 ′-bis(diphenylphosphine)-ferrocene)palladium(II) chloride-dichloromethane complex and 2.3 g of potassium acetate are dissolved in 60 ml of DMSO. The solution is degassed with argon and heated at 95° C. for 2.5 hours. For workup, 600 ml of water are added, the mixture is extracted several times with dichloromethane and the organic phase is washed with saturated sodium chloride solution and dried using a phase separator cartridge. After the solvent has been distilled off, the crude product is purified by preparative RP-HPLC (0-100% acetonitrile in water (+0.01% trifluoroacetic acid)).

后处理

  1. customThe solution is degassed with argon
  2. additionFor workup, 600 ml of water are added
  3. extractionthe mixture is extracted several times with dichloromethane
  4. washthe organic phase is washed with saturated sodium chloride solution
  5. customdried
  6. distillationAfter the solvent has been distilled off
  7. customthe crude product is purified by preparative RP-HPLC (0-100% acetonitrile in water (+0.01% trifluoroacetic acid))

来源与证据

ORD记录
ord-ae34da666d0c49ec9f96cd03cabe9afb
来源数据集
uspto-grants-2010_06
专利号
US07727989B2

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