1,2-Dimethoxyethane → HCID 58255627, compound

HRID 1623519Notes

Reaction equation

HRID 1623519 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH3:12])[C:6](=[O:13])[CH2:5]2.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16](B(O)O)[CH:15]=1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.[Cl-].[Na+].O.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>[CH2:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:16]3[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)[CH2:5][C:6]1=[O:13])[CH3:12]

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 11459089HCID 11459089, compound

Product 1

HCID 58255627HCID 58255627, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

To 5-bromo-1-ethyl-1,3-dihydro-indol-2-one (CAS#41192-37-4, 100 mg, 0.42 mmol) was added 3-pyridine boronic acid (CAS#1692-25-7, 50.2 mg, 0.41 mmol), 1,2-dimethoxyethane (2.5 mL), and 2 M aqueous sodium carbonate (0.410 mL, 0.82 mmol). The reaction mixture was degassed and placed under an argon atmosphere, at which time tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.026 mmol)] was added. The reaction vessel was sealed and was heated by microwave irradiation at 100° C. for 45 minutes. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and brine and the layers were separated. The aqueous layer was extracted two times with ethyl acetate, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 10 to 100%) to afford 1-ethyl-5-pyridin-3-yl-1,3-dihydro-indol-2-one; HRMS: (ESI) m/z 239.1190 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 1.32 (t, J=7.2 Hz, 3H), 3.61 (s, 2H), 3.83 (q, J=7.3 Hz, 2H), 6.96 (d, J=8.1 Hz, 1H), 7.38 (dd, J=7.3, 4.8 Hz, 1H), 7.46-7.57 (m, 2H), 7.78-7.95 (m, 1H), 8.58 (dd, J=4.7, 1.4 Hz, 1H), 8.83 (d, J=1.8 Hz, 1H).

Workup

  1. customThe reaction mixture was degassed
  2. additionwas added
  3. customThe reaction vessel was sealed
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted two times with ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 10 to 100%)

Sources & evidence

ORD record
ord-0906ff1b1f2a4a2da0ed13393a9d5814
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

Loading…