Sodium Carbonate → HCID 86699870, compound

HRID 1772143Notes

Reaction equation

HRID 1772143 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:4]([N+:17]([O-:19])=[O:18])[C:3]1=[O:20].[C:21]([O:24][CH2:25][C:26]1[C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][CH:29]=[CH:28][C:27]=1[N:41]1[CH2:49][C:48]2[C:43](=[CH:44][CH:45]=[C:46]([C:50]([CH3:53])([CH3:52])[CH3:51])[CH:47]=2)[C:42]1=[O:54])(=[O:23])[CH3:22].C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C(OCC)(=O)C.O>[C:21]([O:24][CH2:25][C:26]1[C:31]([C:6]2[CH:5]=[C:4]([N+:17]([O-:19])=[O:18])[C:3](=[O:20])[N:2]([CH3:1])[CH:7]=2)=[CH:30][CH:29]=[CH:28][C:27]=1[N:41]1[CH2:49][C:48]2[C:43](=[CH:44][CH:45]=[C:46]([C:50]([CH3:53])([CH3:52])[CH3:51])[CH:47]=2)[C:42]1=[O:54])(=[O:23])[CH3:22]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 866979362-(5-tert-Butyl-1-oxoisoindolin-2-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl AcetateHCID 86699869HCID 86699869, compound

Product 1

HCID 86699870HCID 86699870, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A 100-mL three-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 122b (560 mg, 2.00 mmol), 103f (830 mg, 2.00 mmol), sodium carbonate (848 mg, 8.00 mmol), dioxane (30 mL) and water (6 mL). This mixture was degassed with nitrogen for 15 min. Tetrakis(triphenyl-phosphine)palladium (231 mg, 0.200 mmol) was added. After heating at 100° C. for 5 h, the reaction mixture was cooled to room temperature and diluted with ethyl acetate (200 mL). The resulting mixture was washed with saturated aqueous sodium bicarbonate (30 mL) and brine (30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography on silica gel to afford an 81% yield (800 mg) of 122c as a crude product, which was used in next step without further purification.

Workup

  1. customA 100-mL three-neck round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. customThis mixture was degassed with nitrogen for 15 min
  4. temperaturethe reaction mixture was cooled to room temperature
  5. washThe resulting mixture was washed with saturated aqueous sodium bicarbonate (30 mL) and brine (30 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-73c558e6565e4aecaa30702e777b2173
Source dataset
uspto-grants-2016_02
Patent number
US09249123B2

Reaction notes

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