Dimethyl Sulfoxide → HCID 59373957, compound

HRID 473746Notes

Reaction equation

Cl[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>O>[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:2]2[N:12]=[CH:11][CH:10]=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a 150 mL pressure vessel was added ethyl 2-chloronicotinate (3.1 g, 17 mmol), 4-(pyridin-2-ylamino)phenol (3.14 g, 17 mmol), and cesium carbonate (5.8 g, 18 mmol) followed by DMSO. The solution was sealed and heated to 100° C. for 20 h. It was cooled and diluted with water and extracted five times with ethyl acetate. The combined organic were washed with brine, dried over sodium sulfate, filtered, and concentrated to a dark brown residue. The residue was taken up in dichlormethane and adsorbed onto silica gel before being purified with flash chromatography (0 to 50% ethyl acetate:hexanes), affording the product as a pale orange solid. MS (ESI, pos. ion) m/z: 336.0 (M+1).

Workup

customThe solution was sealed
temperatureIt was cooled
extractionextracted five times with ethyl acetate
washThe combined organic were washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated to a dark brown residue
custombefore being purified with flash chromatography (0 to 50% ethyl acetate:hexanes)

Sources & evidence

ORD record: ord-3fecc9649c0a4a039dd9b3594e026bc2
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637500B2

Reaction notes

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