Potassium Carbonate → HCID 86672218, compound

HRID 79443

Reaction equation

HRID 79443 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 86672218HCID 86672218, compoundYield 443.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-53f579201ceb48ef92b88f31bb24184f
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Linked notes

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