Cesium carbonate → HCID 59259724, compound
Reaction equation
Br[C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][CH:6]=1.[O:10]1[CH2:15]COC[CH2:11]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[CH3:11][O:10][CH2:15][C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][CH:6]=1Participants
Conditions
- Temperature
- 100 °C
Procedure
A mixture of potassium methoxymethyl trifluoroborate (33 mg, 0.22 mmol), 2-bromo-5-nitrothiophene (30 mg, 0.14 mmol), 1,4-dioxane (1.5 ml), water (0.15 ml), cesium carbonate (235 mg, 0.72 mmol), palladium (II) acetate (3.2 mg, 0.014 mmol), and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (9.0 mg, 0.014 mmol) was stirred at 100° C. (external temperature) for 6 hours. After the reaction mixture was cooled at room temperature, water and ethyl acetate were added to the mixture, followed by filtration using Celite. The organic layer was washed with an aqueous saturated sodium chloride solution, and the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1) to obtain the title compound (2.7 mg, 0.016 mmol, 11%).
Workup
- temperatureAfter the reaction mixture was cooled at room temperature
- filtrationfollowed by filtration
- washThe organic layer was washed with an aqueous saturated sodium chloride solution
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1)
Sources & evidence
- ORD record
- ord-f554aa7f642a4c47944949564482c0f0
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07696347B2
Reaction notes
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