Potassium Carbonate → HCID 86628676, compound

HRID 1807816Notes

Reaction equation

HRID 1807816 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([C:24]1[S:28][C:27]([S:29]([NH:32][C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:31])=[O:30])=[C:26](B(O)O)[CH:25]=1)[CH:21]([CH3:23])[CH3:22].Br[C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][CH:48]=1)[CH:44]=[O:45].C(=O)([O-])[O-].[K+].[K+]>COCCOC.[OH-].[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O.C(O)C>[CH:44]([C:43]1[CH:42]=[C:41]([C:26]2[CH:25]=[C:24]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:28][C:27]=2[S:29]([NH:32][C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:31])=[O:30])[CH:48]=[CH:47][CH:46]=1)=[O:45]

Participants

11

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 765833-BromobenzaldehydeHCID 11484000(2-(N-(tert-Butyl)sulfamoyl)-5-isobutylthiophen-3-yl)boronic acid

Product 1

HCID 86628676HCID 86628676, compoundYield 82%

Reagents, catalysts & solvents 6

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

Palladium acetate (84.6 mg, 0.38 mmol) and triphenylphosphine (0.40 g, 1.52 mmol) in DME (5 mL) were stirred for 30 min under N2(g). The catalyst was then transferred into a nitrogen-flushed mixture of 5-iso-butyl-2-(N-tert-butylaminosulfonyl)thiophene-3-boronic acid (4.0 g, 12.56 mmol, see step (c) above), 3-bromobenzaldehyde (2.96 g, 25.12 mmol) and potassium carbonate (5.21 g, 37.7 mmol) in a solvent mixture of DME (28 mL), ethanol (8 mL), and water (12 mL). After stirring for 20 h at reflux under a N2 atmosphere, the reaction mixture was diluted with NaOH (1M solution, 50 mL) followed by ethyl acetate (150 mL). The organic layer was washed with water, and brine, dried (over anhydrous MgSO4), concentrated in vacuo, and the residue subjected to flash chromatography (20% ethyl acetate in petroleum ether, 230-400 mesh) to afford the title compound as colourless solid (3.9 g, 10.3 mmol, 82%).

Workup

  1. customflushed
  2. temperatureat reflux under a N2 atmosphere
  3. washThe organic layer was washed with water, and brine
  4. dry with materialdried (over anhydrous MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b5febe9a915425cba3296f05d4c641c
Source dataset
uspto-grants-2013_01
Patent number
US08357710B2

Reaction notes

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