Pyridine → Methyl 2-(5-bromopyridin-3-yl)acetate

HRID 2362359Notes

Reaction equation

HRID 2362359 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[N:6][CH:7]=1.S(Cl)(Cl)=O.N1C=CC=C[CH:17]=1>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:17])=[O:10])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 28025392-(5-Bromopyridin-3-yl)acetic acid

Product 1

HCID 23398394Methyl 2-(5-bromopyridin-3-yl)acetateYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(5-bromopyridin-3-yl)acetic acid (5.00 g, 23.14 mmol) in methanol (55 mL) at 0° C. was added thionyl chloride (2.196 mL, 30.1 mmol) slowly, pyridine (2.434 mL, 30.1 mmol) was added slowly after and the reaction was stirred at room temperature overnight. Solvent was removed in vacuo and the residue was diluted with water and extracted with ethyl acetate, the organics was washed with brine, dried over magnesium sulfate, filtered and concentrated. Biotage purification (35% EtOAc/Hex) gave title compound (4.73 g, 20.6 mmol, 89% yield). 1H-NMR (CDCl3, 500 MHz) δ 8.63 (d, J=2.14 Hz, 1H), 8.47 (d, J=1.83 Hz, 1H), 7.84 (dd, J=2.14, 1.83 Hz, 1H), 3.76 (s, 3H), 3.65 (s, 2H). Mass spec.: 230.9 (MH)+.

Workup

  1. customSolvent was removed in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washthe organics was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customBiotage purification (35% EtOAc/Hex)

Sources & evidence

ORD record
ord-425356a58ccb4e6d9ddc7da31850e806
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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