Sodium Carbonate → N-methoxy-N-methyl-3-(3'-methylsulfanyl-biphenyl-4-yl)-acrylamide

HRID 2207866Notes

Reaction equation

HRID 2207866 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([N:12]([O:14][CH3:15])[CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:16][S:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=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:5]1[CH:6]=[CH:7][C:2]([C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([S:17][CH3:16])[CH:23]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343833-(Methylthio)benzeneboronic acidHCID 713762353-(4-Bromophenyl)-N-methoxy-N-methylprop-2-enamide

Product 1

HCID 131735932N-methoxy-N-methyl-3-(3'-methylsulfanyl-biphenyl-4-yl)-acrylamideYield 125.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3-(4-Bromo-phenyl)-N-methoxy-N-methyl-acrylamide (11.7 g, 43.2 mmol) prepared in Step 1 of Preparation 1, 3-(methylthio)phenylboronic acid (14.5 g, 86.4 mmol), Pd(PPh3)4 (2.5 g, 2.2 mmol) and sodium carbonate (13.7 g, 129.6 mmol) were added to a mixed solvent of N,N-dimethylformamide (200.0 mL) and distilled water (50.0 mL). The reaction mixture was stirred at 80° C. for 7 hours and then extracted with ethyl acetate. The extract was washed with a saturated solution of ammonium chloride, 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=1/5) to give 17.0 g of the titled compound as a yellow solid.

Workup

  1. distillationdistilled water (50.0 mL)
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with a saturated solution of ammonium chloride
  4. dry with materialdried on anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow liquid residue
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5)

Sources & evidence

ORD record
ord-18cc36b31b1f4761be4fe3366667220a
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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