Cesium carbonate → 6-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-[(5-chloropyridin-3-yl)oxy]nicotinonitrile

HRID 916981Notes

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].[Cl:24][C:25]1[CH:26]=[C:27]([OH:31])[CH:28]=[N:29][CH:30]=1.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:31][C:27]2[CH:28]=[N:29][CH:30]=[C:25]([Cl:24])[CH:26]=2)[N:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To the product of Example 131 (100 mg, 0.2793 mmol) was added 5-chloro-3-pyridinol (181 mg, 1.397 mmol), Cs2CO3 (228 mg, 0.6983 mmol) and toluene (1.5 mL) before heating to 100° C. After stirring 14 hours the reaction solution was filtered and concentrated. The residue was purified by flash chromatography (silica gel) eluting with a gradient of 1 to 3% ethyl acetate/dichloromethane affording the product. MS (electrospray) m/e 453.9 MH+ (Rt=4.1 min LC/MS).

Workup

filtrationwas filtered
concentrationconcentrated
customThe residue was purified by flash chromatography (silica gel)
washeluting with a gradient of 1 to 3% ethyl acetate/dichloromethane affording the product

Sources & evidence

ORD record: ord-11df50f761bc4f909a1abe052d35825d
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271266B2

Reaction notes

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