Potassium Carbonate → HCID 66930005, compound

HRID 2261224Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)=[O:4].Br[C:15]1[CH:16]=[CH:17][C:18]([C:21]#[N:22])=[N:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O.CCOC(C)=O>[C:21]([C:18]1[N:19]=[CH:20][C:15]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)=[CH:16][CH:17]=1)#[N:22]

Participants

Conditions

Temperature: 80 °C

Procedure

4-Methoxycarbonylphenyl boronic acid (0.5 g) and 5-bromo-2-pyridinecarbonitrile (0.5 g) in a mixture of THF (5 ml) and water (5 ml) were treated with tetrakis(triphenyl phosphine)palladium(0) (0.32 g) and potassium carbonate (1 g). A further amount of THF (5 ml) was added and the reaction was heated at 80° C. for 1 h. After cooling the reaction mixture was diluted with EtOAc (30 ml) and washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried (magnesium sulfate) and concentrated to give a crude residue that was purified by column chromatography (silica-gel, gradient 0-100% EtOAc in hexane) to give the title compound (D8) as a white solid (0.5 g). LCMS electrospray (+ve) 239 (MH+).

Workup

temperatureAfter cooling the reaction mixture
washwashed with saturated aqueous sodium hydrogen carbonate solution
dry with materialThe organic layer was dried (magnesium sulfate)
concentrationconcentrated
customto give a crude residue that
customwas purified by column chromatography (silica-gel, gradient 0-100% EtOAc in hexane)

Sources & evidence

ORD record: ord-ae996f6ba89f4e13b96cde055a5c4bb4
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846922B2

Reaction notes

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