Potassium Carbonate → HCID 88996204, compound

HRID 591059Notes

Reaction equation

HRID 591059 reaction equation
Cl[C:2]1[N:3]([CH3:10])[C:4](=[O:9])[S:5][C:6]=1[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+].CC1(C)C(C)(C)OB([C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[O:31][CH2:30][CH2:29][CH2:28]3)O1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)C.O.C(OCC)(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[O:31]1[C:32]2[CH:33]=[CH:34][C:25]([C:2]3[N:3]([CH3:10])[C:4](=[O:9])[S:5][C:6]=3[CH:7]=[O:8])=[CH:26][C:27]=2[CH:28]=[CH:29][CH2:30]1

Participants

9

Reactant 3

HCID 11430Potassium CarbonateHCID 1223938157805-14-8HCID 438110342-(3,4-dihydro-2H-1-benzopyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 88996204HCID 88996204, compoundYield 35%

Reagents, catalysts & solvents 5

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere, a solution of 4-chloro-3-methyl-2-oxo-2,3-dihydro-thiazole-5-carbaldehyde (33b) (500 mg, 2.82 mmol), potassium carbonate (390 mg, 2.82 mmol), palladium diacetate (100 mg, 0.48 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (732 mg, 2.82 mmol) and tetrabutylammonium bromide (910 mg, 2.82 mmol) in ethanol (7 mL) and water (10 mL) was stirred at 70° C. for 3 hours. The mixture was then cooled at room temperature and diluted with ethyl acetate (30 mL) and water (30 mL). The organic layer was washed with water (30 mL), brine (30 mL), dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20) to afford the desired product as a white solid (270 mg, 0.98 mmol, 35%).

Workup

  1. washThe organic layer was washed with water (30 mL), brine (30 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20)

Sources & evidence

ORD record
ord-38a5bd20ec2245448de512248448351a
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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