Potassium Carbonate → HCID 86302075, compound
Reaction equation
BrC1C=C[C:5]([O:8]C)=CC=1C(=O)C(C)CC.N1CCC[C@H]1C(O)=O.[C:24]([O-:27])([O-])=O.[K+].[K+].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[N-]=[N+]=[N-].[Na+].[CH2:47]([C:49]1([CH3:61])[C:57](=[O:58])[C:56]2[C:51](=[CH:52][CH:53]=[C:54]([O:59][CH3:60])[CH:55]=2)[NH:50]1)[CH3:48]>CS(C)=O.O.[O-]S([O-])(=O)=O.[Cu+2]>[CH2:47]([C:49]1([CH3:61])[C:57](=[O:58])[C:56]2[C:51](=[C:52]([O:27][CH3:24])[C:53]([O:8][CH3:5])=[C:54]([O:59][CH3:60])[CH:55]=2)[NH:50]1)[CH3:48]Participants
10
Reactant 6
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 1-(2-bromo-5-methoxyphenyl)-2-methylbutan-1-one (0.1 g, 3.68 mmol) in DMSO, were added L-proline (8.49 mg, 0.73 mmol), K2CO3 (76.42 mg, 5.53 mmol), CuSO4:5H2O (14.61 mg, 0.73 mmol), sodium ascorbate (14.61 mg, 0.73 mmol), and NaN3 (28.77 mg, 4.42 mmol). The mixture was stirred for 17 h at 70° C. (oil bath temperature). The reaction mixture was diluted with 30 mL of water and extracted with ethyl acetate (3×30 mL). Combined organic layer was dried (Na2SO4) and evaporated under reduced pressure. The crude was purified over silica gel (ethyl acetate and pet ether as eluent) to procure 2g (0.053 g, 2.58 mmol) in 69% yields.
Workup
- extractionextracted with ethyl acetate (3×30 mL)
- dry with materialCombined organic layer was dried (Na2SO4)
- customevaporated under reduced pressure
- customThe crude was purified over silica gel (ethyl acetate and pet ether as eluent)
- customyields
Sources & evidence
- ORD record
- ord-540b1c7f0f96462fb4eb6b6f1e9ec569
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09145364B2
Reaction notes
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