Potassium Carbonate → HCID 9795926, compound

HRID 1167227Notes

Reaction equation

HRID 1167227 reaction equation
[CH3:1][CH:2]([CH3:16])[CH2:3][NH:4][C:5](=[O:15])[CH:6]([C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=1)[CH3:7].[S:17]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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>[CH3:1][CH:2]([CH3:16])[CH2:3][NH:4][C:5](=[O:15])[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([C:19]2[CH:20]=[CH:21][S:17][CH:18]=2)=[CH:10][CH:9]=1)[CH3:7]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 581760Thiophene-3-boronic acidHCID 22996532HCID 22996532, compound

Product 1

HCID 9795926HCID 9795926, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of N-2-methylpropyl-2-(4-bromophenyl)2-methylacetamide 1.1 g (3.9 mmol, part B above), 0.7 g (5.8 mmol) of thiophene-3-boronic acid and 0.8 g (5.8 mmol) of potassium carbonate in 12 mL of 3:1 dioxane/water was added 0.2 g (0.2 mmol) of tetrakis(triphenylphosphine)palladium. The mixture was heated to reflux for 16 hours, cooled and diluted with 10 mL of water. The mixture was extracted three times with 10 mL each of dichloromethane. The combined organics were dried (Na2SO4), filtered and concentrated in vacuo. Chromatography (65 g of silica gel, 35% ethyl acetate/hexanes) of the residue afforded 0.3 g (31%) of the final title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 16 hours
  3. temperaturecooled
  4. extractionThe mixture was extracted three times with 10 mL each of dichloromethane
  5. dry with materialThe combined organics were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28232608757c4cc19a55d6f6a186b02f
Source dataset
uspto-grants-2003_09
Patent number
US06617351B1

Reaction notes

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