Water → 3-Bromo-6-[(6-isopropoxypyridin-3-yl)oxy]-pyridine

HRID 404925Notes

Reaction equation

HRID 404925 reaction equation
[CH:1]([O:4][C:5]1[N:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[Br:12][C:13]1[CH:14]=[CH:15][C:16](F)=[N:17][CH:18]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[Br:12][C:13]1[CH:18]=[N:17][C:16]([O:11][C:8]2[CH:9]=[N:10][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:6][CH:7]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27831685-Bromo-2-fluoropyridineHCID 580424216-Isopropoxypyridin-3-OL

Product 1

HCID 694358573-Bromo-6-[(6-isopropoxypyridin-3-yl)oxy]-pyridineYield 39%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The mixture of Example 68B (1.0821 g, 7.064 mmol), 5-bromo-2-fluoropyridine (1.245 g, 7.074 mmol, 1.0 eq.), and K2CO3 (1.17 g, 8.47 mmol, 1.2 eq.) in dimethylsulfoxide (8 mL) was heated to 160° C. under microwave for 30 min. The reaction mixture was poured into water. The aqueous layer was extracted with ether (1×). The ether layer was washed with 10% NaOH (1×), brine (1×), dried over MgSO4, filtered and concentrated. The product was purified on silica gel eluting with ethyl acetate: hexane gradient to give the desired product as a solid (0.845 mg, 39%).

Workup

  1. extractionThe aqueous layer was extracted with ether (1×)
  2. washThe ether layer was washed with 10% NaOH (1×), brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-eaf22ee23b234f48877c7cd678a4c5fe
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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