Potassium Carbonate → HCID 66974560, compound

HRID 2090776Notes

Reaction equation

HRID 2090776 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][C:13]([CH2:22][N:23]([CH3:31])C(=O)OC(C)(C)C)=[CH:12]2)(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1.[CH3:32]B(O)O.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+].C(OCC)(=O)C.[ClH:53]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[ClH:53].[ClH:53].[CH3:31][NH:23][CH2:22][C:13]1[CH:14]=[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]([S:8]([C:4]2[CH:5]=[N:6][CH:7]=[C:2]([CH3:32])[CH:3]=2)(=[O:9])=[O:10])[CH:12]=1

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 66974640HCID 66974640, compound

Product 1

HCID 66974560HCID 66974560, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Under an argon atmosphere, a mixture of tert-butyl ({1-[(5-bromopyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl)methylcarbamate (112 mg), methylboronic acid (18 mg), tetrakis(triphenylphosphine)palladium (23 mg), potassium carbonate (138 mg) and 1,4-dioxane (5 mL) was stirred at 80° C. for one day. The reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→1:1) to give an oil. The oil was dissolved in ethanol (1 mL), and a 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added. After stirring at room temperature for 1 hr, the mixture was concentrated under reduced pressure. The residue was recrystallized from ethanol-ethyl acetate to give the title compound as a colorless solid (yield 32.6 mg, 39%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→1:1)
  6. customto give an oil
  7. stirringAfter stirring at room temperature for 1 hr
  8. concentrationthe mixture was concentrated under reduced pressure
  9. customThe residue was recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-f5371bcba31146e5be5e596aefdd5b1c
Source dataset
uspto-grants-2013_05
Patent number
US08436187B2

Reaction notes

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