Cesium carbonate → 5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(4-fluorophenylthio)nicotinonitrile

HRID 916939

Reaction equation

Cl[C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:7]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[Cs+].[Cs+].[F:31][C:32]1[CH:37]=[CH:36][C:35]([SH:38])=[CH:34][CH:33]=1>C1(C)C=CC=CC=1>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:7]2[C:8]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])=[N:9][C:2]([S:38][C:35]3[CH:36]=[CH:37][C:32]([F:31])=[CH:33][CH:34]=3)=[C:3]([CH:6]=2)[C:4]#[N:5])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 100 °C

Procedure

An oven-dried round bottom flask was charged with 60.0 mg (0.152 mmol) of the product of Example 36 and Cs2CO3 (250.0 mg, 0.767 mmol), toluene (1.0 mL) and 4-fluorobenzene thiol (97.5 mg, 0.761 mmol) were added sequentially. The reaction was heated to 100° C. for 23 hours and then allowed to cool to room temperature at which point the reaction was filtered and concentrated. The residue was purified by preparative thin layer chromatography (20 cm×20 cm, 1000 μm, silica gel) eluting with 10:90 EtOAc-hexane affording a white solid). MS (electrospray) m/e 487 MH+.

Workup

additionwere added sequentially
temperatureto cool to room temperature at which
filtrationwas filtered
concentrationconcentrated
customThe residue was purified by preparative thin layer chromatography (20 cm×20 cm, 1000 μm, silica gel)
washeluting with 10:90 EtOAc-hexane affording a white solid)

Sources & evidence

ORD record: ord-8914b0d84d26416787fa26fdeba3d078
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271266B2

Linked notes

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