Potassium Carbonate → HCID 57672522, compound

HRID 2101790Notes

Reaction equation

HRID 2101790 reaction equation
Br[C:2]1[CH:3]=[C:4]([C@H:16]([CH2:22][CH2:23][CH3:24])[CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:25](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>CN(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>[CH3:25][C:2]1[CH:3]=[C:4]([C@H:16]([CH2:22][CH2:23][CH3:24])[CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 57672488HCID 57672488, compound

Product 1

HCID 57672522HCID 57672522, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a flask charged with 27.2 (0.8986 g, 2.30 mmol), tetrakis(triphenylphosphine)palladium (0) (0.265 g, 0.230 mmol), and potassium carbonate (0.635 g, 4.59 mmol) in DMF (10 mL) was added trimethylboroxine (0.959 mL, 6.89 mmol). The resulting mixture was then heated at 100° C. overnight. The reaction was allowed to cool and was then filtered and concentrated. The product was purified by silica gel chromatography (0 to 20% EtOAc/Hexanes) yielding 27.3 (0.46 g, 61% yield).

Workup

  1. temperatureto cool
  2. filtrationwas then filtered
  3. concentrationconcentrated
  4. customThe product was purified by silica gel chromatography (0 to 20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-9347260d247c40b2934eb2e836257c31
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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