Cesium carbonate → HCID 24985290, compound

HRID 2101818Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:19][C:20]1[N:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[O:22][N:21]=1>CN(C=O)C>[F:33][C:31]([F:32])([F:34])[C:27]1[CH:26]=[C:25]([C:23]2[O:22][N:21]=[C:20]([CH2:19][N:1]3[C:9]4[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=4)[CH:3]=[CH:2]3)[N:24]=2)[CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 1H-indole-5-carbonitrile (0.05 g, 0.35 mmol) in anhydrous DMF (2 mL) was added Cs2CO3 (0.18 g, 0.55 mmol) and 3-(chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole (0.14 g, 0.55 mmol). The mixture was heated at 90° C., under N2, for 30 min. Upon cooling, the mixture was partitioned between Et2O and H2O. The aqueous phase was extracted with Et2O (×2). The combined organic phases were washed with sat'd brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (2-20% EtOAc-hexanes gradient) and the product crystallized from CH2Cl2-hexanes to afford the title compound as a white solid (0.1 g, 78% yield): MS (ES) m/z 369 (M+1).

Workup

temperatureUpon cooling
customthe mixture was partitioned between Et2O and H2O
extractionThe aqueous phase was extracted with Et2O (×2)
washThe combined organic phases were washed with sat'd brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (2-20% EtOAc-hexanes gradient)
customthe product crystallized from CH2Cl2-hexanes

Sources & evidence

ORD record: ord-17ab2ebdb26b484fb15183b77f81cd9d
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572820B2

Reaction notes

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