Potassium Carbonate → N-(1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)-7-(5-formylfuran-2-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79443

반응식

HRID 79443 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 86672218N-(1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)-7-(5-formylfuran-2-yl)imidazo[1,2-a]pyridine-3-carboxamide수율 443.3%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

반응 조건

온도
65 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-53f579201ceb48ef92b88f31bb24184f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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