Potassium Carbonate → HCID 86672218、化合物

HRID 79443

反応式

HRID 79443 の反応式
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

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 27343555-Formylfuran-2-boronic acidHCID 23677046Sodium 2'-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonateHCID 68333436HCID 68333436、化合物

生成物 1

HCID 86672218HCID 86672218、化合物収率 443.3%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
65 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-53f579201ceb48ef92b88f31bb24184f
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

関連ノート

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