碳酸钾 → HCID 86672218，化合物

HRID 79443

反应方程式

HRID 79443 反应方程式
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[C:16]([CH2:31][CH3:32])=[N:17][N:18]4[CH2:23][C:24]3[CH:28]=[C:27]([CH3:29])[N:26]([CH3:30])[N:25]=3)=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2[C:51]([O:52]C)=[CH:50][CH:49]=[C:48](S([O-])(=O)=O)[C:47]=2[O:58]C)CCCCC1.[Na+].C(=O)([O-])[O-].[K+].[K+].C(C1OC(B(O)O)=CC=1)=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[CH3:30][N:26]1[C:27]([CH3:29])=[CH:28][C:24]([CH2:23][N:18]2[C:19]3[C:15](=[C:14]([NH:13][C:11]([C:8]4[N:5]5[CH:6]=[CH:7][C:2]([C:47]6[O:58][C:50]([CH:51]=[O:52])=[CH:49][CH:48]=6)=[CH:3][C:4]5=[N:10][CH:9]=4)=[O:12])[CH:22]=[CH:21][CH:20]=3)[C:16]([CH2:31][CH3:32])=[N:17]2)=[N:25]1

参与物

7

反应物 4

HCID 11430碳酸钾HCID 27343555-甲醛基呋喃-2-硼酸HCID 236770462'-二环己基-2,6-二甲氧基-3-磺酸- 1,1'-联苯水合物钠盐HCID 68333436HCID 68333436，化合物

产物 1

HCID 86672218HCID 86672218，化合物收率 443.3%

试剂、催化剂与溶剂 2

HCID 167845palladium acetate催化剂HCID 312751,4-二氧六环溶剂

反应条件

温度
65 °C

实验过程

A round bottom flask was charged with 7-bromo-N-(1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (Preparation H; 100 mg, 0.20 mmol), sodium 2′-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonate (8.3 mg, 0.016 mmol), potassium carbonate (93 mg, 0.67 mmol), palladium acetate (1.8 mg, 0.008 mmol), and 5-formylfuran-2-ylboronic acid (57 mg, 0.4 mmol). To the flask was added a 5:1 dioxane:water mixture (3 mL), the reaction mixture was degassed under nitrogen, and stirred at 65° C. for 10 hours. The reaction mixture was cooled, diluted with water, and extracted multiple times with DCM and EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate, and concentrated under vacuum. The crude product was subjected to preparative thin-layer chromatography on silica with 10% MeOH-DCM as eluent to afford the product (36 mg) as a yellow solid.

后处理

  1. customwater mixture (3 mL), the reaction mixture was degassed under nitrogen
  2. temperatureThe reaction mixture was cooled
  3. additiondiluted with water
  4. extractionextracted multiple times with DCM and EtOAc
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum

来源与证据

ORD记录
ord-53f579201ceb48ef92b88f31bb24184f
来源数据集
uspto-grants-2014_09
专利号
US08841455B2

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