Potassium Carbonate → 3-Bromo-5-(4-(pyrrolidine-1-sulfonyl)phenoxy)pyridine

HRID 2212138

Reaction equation

HRID 2212138 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.F[C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][C:10]2[CH:15]=[CH:14][C:13]([S:16]([N:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)(=[O:18])=[O:17])=[CH:12][CH:11]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5995293-Bromo-5-hydroxypyridineHCID 7965781-(4-Fluorobenzenesulfonyl)pyrrolidine

Product 1

HCID 219640953-Bromo-5-(4-(pyrrolidine-1-sulfonyl)phenoxy)pyridineYield 59.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-bromo-3-pyridinol (2.61 g, 15 mmol), dimethylacetamide (50 mL), 1-((4-fluorophenyl)sulfonyl)pyrrolidine (5.8 g, 25 mmol) and potassium carbonate (4.1 g, 30 mmol) was heated at 120° C. for 18 h, then cooled to room temperature and concentrated by rotary evaporation. The residue was dissolved in ethyl acetate (200 mL) and the organic phase washed with water (3×100 mL) and brine (100 mL), then dried (MgSO4), filtered and concentrated by rotary evaporation. The crude product was purified by column chromatography, eluting with ethyl acetate/cyclohexane (20/80, v/v). Selected fractions containing the product were concentrated via rotary evaporation to give 3.4 g (59%) of a red solid (m.p. 148° C.)

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated by rotary evaporation
  3. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  4. washthe organic phase washed with water (3×100 mL) and brine (100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customThe crude product was purified by column chromatography
  9. washeluting with ethyl acetate/cyclohexane (20/80
  10. additionSelected fractions containing the product
  11. concentrationwere concentrated via rotary evaporation

Sources & evidence

ORD record
ord-3c5af9c391014883b283a8713acbd156
Source dataset
uspto-grants-2006_09
Patent number
US07101896B2

Linked notes

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