Water ethylacetate → HCID 86707865, compound

HRID 922453Notes

Reaction equation

HRID 922453 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:10]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.O.[C:17]([O:20][CH2:21][CH3:22])(=O)[CH3:18]>C1(C)C=CC=CC=1.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>[CH2:21]([O:20][C:17]([C:2]1[CH:3]=[C:4]2[N:10]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1)=[CH2:18])[CH3:22]

Participants

5

Reactant 2

HCID 22728543Water ethylacetateHCID 68784063HCID 68784063, compound

Product 1

HCID 86707865HCID 86707865, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6-bromo-1-(3-methoxypropyl)-1H-pyrrolo[3,2-b]pyridine (1.5 g) in toluene (30 mL) were added tri-n-butyltin-1-ethoxyvinyl (5.65 mL) and dichlorobis(triphenylphosphine)palladium (II) (782 mg), and the mixture was heated to stir at 110° C. for 30 minutes. The reaction solution was cooled to room temperature, and then thereto was added water-ethyl acetate, and an insoluble was filtered through Celite. The organic layer was separated, and then washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1→1/1) to give 6-(1-ethoxyvinyl)-1-(3-methoxypropyl)-1H-pyrrolo[3,2-b]pyridine [REx(23-2)] (1.69 g) as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe reaction solution was cooled to room temperature
  3. filtrationan insoluble was filtered through Celite
  4. customThe organic layer was separated
  5. washwashed with saturated saline
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1→1/1)

Sources & evidence

ORD record
ord-37ee25a27b1a4f4caecae929eeafbe28
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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