Potassium Carbonate → HCID 58282689, compound

HRID 880817Notes

Reaction equation

HRID 880817 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[N:9]2)[N:5]=[C:4]([O:17][CH3:18])[CH:3]=1.C([SH:23]1(CCCC)(CCCC)[CH:27]=[C:26]([CH:28]([CH3:30])[CH3:29])[N:25]=[CH:24]1)CCC.[SnH4].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:18][O:17][C:4]1[CH:3]=[C:2]([C:24]2[S:23][CH:27]=[C:26]([CH:28]([CH3:30])[CH3:29])[N:25]=2)[N:7]=[C:6]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[N:9]2)[N:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 58282711HCID 58282711, compoundHCID 178454982HCID 178454982, compound

Product 1

HCID 58282689HCID 58282689, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of compound 305 (892 mg, 3.2 mmol) in dry DMF (15 mL) were added tributyl(4-isopropyl-thiazole)-stannane (2 g, 4.8 mmol), PdCl2(PPh3)2 (224 mg, 0.32 mmol), and potassium carbonate (530 mg, 3.84 mmol). The mixture was stirred at 90° C. for 48 hrs, and the concentrated under reduced pressure. Water and ethyl acetate were added. Organics were washed with water, dried over Na2SO4, filtered, concentrated under reduced pressure, and purified by silica gel chromatography to yield compound 307h as a beige solid in 76% yield. MS (ESI, EI+) m/z=370 (MH+).

Workup

  1. concentrationthe concentrated under reduced pressure
  2. additionWater and ethyl acetate were added
  3. washOrganics were washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-842a6da2d4d6472582393e8f65b022a4
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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