Cesium carbonate → 5-Chloro-2-{[4-(methylsulfonyl)phenyl]oxy}pyridine

HRID 32384

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[CH3:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11].C([O-])([O-])=O.[Cs+].[Cs+]>CN1C(=O)CCC1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([O:19][C:16]2[CH:15]=[CH:14][C:13]([S:10]([CH3:9])(=[O:12])=[O:11])=[CH:18][CH:17]=2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 170 °C

Procedure

2,5-dichloropyridine (1.48 g; 10 mmol), 4-methylsulfonylphenol (1.89 g; 11 mmol) and Cs2CO3 (4.24 g; 13 mmol) was slurried in 75 mL of NMP. The slurry was heated to approx 170° C. over night. After cooling the Cs2CO3 was filtered off and the solvent was extracted between H2O and EtOAc. The organic phase was dried over Na2SO4 and evaporated. Heptane:EtOAc 2:1 was added to the residue and the crystalls was filtered off 1.42 g (50%).

Workup

filtrationwas filtered off
extractionthe solvent was extracted between H2O and EtOAc
dry with materialThe organic phase was dried over Na2SO4
customevaporated
additionHeptane:EtOAc 2:1 was added to the residue
filtrationthe crystalls was filtered off 1.42 g (50%)

Sources & evidence

ORD record: ord-b538d16793344b958f75b279f78671ff
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427631B2

Linked notes

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