Methanol → HCID 66974601, compound

HRID 2090775Notes

Reaction equation

HRID 2090775 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.C(N(CC)CC)C.CO.[C:41]([O:44][CH2:45]C)(=[O:43])C.[ClH:47]>C(O)C>[ClH:47].[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]([CH:3]=2)[C:41]([O:44][CH3:45])=[O:43])(=[O:10])=[O:9])[CH:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 21866389Hydrogen chloride-ethyl acetateHCID 66974640HCID 66974640, compound

Product 1

HCID 66974601HCID 66974601, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl ({1-[(5-bromopyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl)methylcarbamate (112 mg), dichloro[bis(triphenylphosphine)]palladium (28 mg), triethylamine (0.25 mL) and methanol (15 mL) was stirred under a carbon monoxide atmosphere (3 atm) at 100° C. for 12 hr. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. A saturated aqueous sodium hydrogencarbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→3:2) to give a colorless oil. The obtained oil was dissolved in ethanol (2 mL), and a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added. After stirring at room temperature for 1 hr, the mixture was concentrated under reduced pressure, and recrystallized from ethanol to give the title compound as a solid (yield 47.0 mg, 56%).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionA saturated aqueous sodium hydrogencarbonate solution was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→3:2)
  9. customto give a colorless oil
  10. stirringAfter stirring at room temperature for 1 hr
  11. concentrationthe mixture was concentrated under reduced pressure
  12. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d3dd49d6efaf4225adae0303e3727ce7
Source dataset
uspto-grants-2013_05
Patent number
US08436187B2

Reaction notes

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