Cesium carbonate → 6-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-(3,4-difluorophenoxy)nicotinonitrile

HRID 916982Notes

Reaction equation

Cl[C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[C:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:6][C:3]=1[C:4]#[N:5].[F:24][C:25]1[CH:26]=[C:27]([OH:32])[CH:28]=[CH:29][C:30]=1[F:31].C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1>[Cl:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:8]1[C:7]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)=[CH:6][C:3]([C:4]#[N:5])=[C:2]([O:32][C:27]2[CH:28]=[CH:29][C:30]([F:31])=[C:25]([F:24])[CH:26]=2)[N:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To the product of Example 131 (250 mg, 0.6984 mmol) was added 3,4-difluorophenol (273 mg, 2.095 mmol), Cs2CO3 (683 mg, 2.096 mmol) and toluene (4.5 mL) before heating to 100° C. After stirring 16 hours the reaction solution was filtered and concentrated. The residue was purified by flash chromatography (silica gel) eluting with 10% ethyl acetate/hexane affording the product. MS (electrospray) m/e 453.0 MH+ (Rt=4.4 min LC/MS).

Workup

filtrationwas filtered
concentrationconcentrated
customThe residue was purified by flash chromatography (silica gel)
washeluting with 10% ethyl acetate/hexane affording the product

Sources & evidence

ORD record: ord-ad9cd9cad4b74bfdb98b72fd0bc7f9af
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271266B2

Reaction notes

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