Potassium Carbonate → N-{5-[3-(2-furanyl)-6-quinoxalinyl]-3-pyridinyl}benzenesulfonamide
Reaction equation
B(O)O.O1[CH:8]=[CH:7][CH:6]=[C:5]1B(O)O.C(=O)([O-])[O-].[K+].[K+].CC1(C)C(C)(C)OB([C:26]2[CH:27]=[C:28]([NH:32][S:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)(=[O:35])=[O:34])[CH:29]=[N:30][CH:31]=2)O1.O1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1>>[O:46]1[CH:47]=[CH:48][CH:44]=[C:45]1[C:29]1[CH:28]=[N:32][C:5]2[C:31]([N:30]=1)=[CH:26][C:8]([C:26]1[CH:27]=[C:28]([NH:32][S:33]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)(=[O:34])=[O:35])[CH:29]=[N:30][CH:31]=1)=[CH:7][CH:6]=2Participants
Conditions
- Temperature
- 100 °C
Procedure
A slurry of 7-bromo-2-chloroquioxaline (0.82 mmol), a boronic acid such as 2-furan boronic acid (0.82 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.06 mmol), in 1,4-dioxane (4 ml) and 2M solution potassium carbonate (2 ml) was stirred at 100° C. for 3 hour. Then N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]benzenesulfonamide (0.90 mmol) was added and the reaction mixture stirred at 100° C. for 18 hours. The reaction was cooled to ambient temperature, the organic layer separated and purified directly on silica by column chromatography (50% ethyl acetate/hexanes). The desired fractions were combined and concentrated to give the title compound (50 mg, 14%) as a tan solid. MS(ES)+ m/e 429.0 [M+H]+.
Workup
- temperatureThe reaction was cooled to ambient temperature
- customthe organic layer separated
- custompurified directly on silica by column chromatography (50% ethyl acetate/hexanes)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ea312eceb9d145bba3ac21a45bcfd633
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592342B2
Reaction notes
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