Cesium carbonate → 2-[3-(Benzyloxy)-4-nitrophenoxy]-5-(methylsulfonyl)pyridine

HRID 1188916Notes

Reaction equation

HRID 1188916 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:18])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][N:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[O:18][C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][N:21]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 98994832-Bromo-5-(methylsulfonyl)pyridineHCID 109777113-(Benzyloxy)-4-nitrophenol

Product 1

HCID 668858722-[3-(Benzyloxy)-4-nitrophenoxy]-5-(methylsulfonyl)pyridineYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(benzyloxy)-4-nitrophenol (31.4 g), 2-bromo-5-(methylsulfonyl)pyridine (30.3 g), cesium carbonate (83.6 g) and N,N-dimethylformamide (300 mL) was stirred at 100° C. for 3 h. The mixture was concentrated under reduced pressure. Water was added to the residue and the resulting brown suspension was filtered to give the title compound (45.6 g, 89%) as a yellow solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. filtrationthe resulting brown suspension was filtered

Sources & evidence

ORD record
ord-dc35f9b748814c8188e6750b951ea4fc
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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