Sodium Carbonate → HCID 131735936, compound

HRID 2207873Notes

Reaction equation

HRID 2207873 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]([N:12]([O:14][CH3:15])[CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH3:16][S:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.CN(C)C=O>[CH3:15][O:14][N:12]([CH3:13])[C:10](=[O:11])[CH:9]=[CH:8][C:4]1[CH:3]=[C:2]([C:21]2[CH:22]=[CH:23][C:18]([S:17][CH3:16])=[CH:19][CH:20]=2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339594-(Methylthio)phenylboronic acidHCID 73014354HCID 73014354, compound

Product 1

HCID 131735936HCID 131735936, compoundYield 104.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3-(3-Bromo-phenyl)-N-methoxy-N-methylacrylamide (14.5 g, 53.7 mmol) prepared in Step 1, 4-(methylthio)phenylboronic acid (18.0 g, 107.4 mmol), Pd(PPh3)4 (3.1 g, 2.7 mmol) and sodium carbonate (17.1 g, 161.1 mmol) were added to a mixed solvent of N,N-dimethylformamide (100.0 mL) and distilled water (10.0 mL). The reaction mixture was stirred at 80° C. for 20 hours, quenched with a saturated solution of ammonium chloride, and then extracted with diethyl ether three times. The combined extract was washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3) to give 17.6 g of the titled compound as a yellow solid.

Workup

  1. distillationdistilled water (10.0 mL)
  2. customquenched with a saturated solution of ammonium chloride
  3. extractionextracted with diethyl ether three times
  4. extractionThe combined extract
  5. washwas washed with brine
  6. dry with materialdried on anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give a yellow liquid residue
  9. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3)

Sources & evidence

ORD record
ord-760be3f681194789a5e7b0cef465dba9
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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