4-Bromo-2-methoxypyridine → Ethyl 2-(2-methoxypyridin-4-yl)acetate

HRID 578895Notes

Reaction equation

HRID 578895 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[Br-].[CH2:11]([O:13][C:14](=[O:17])[CH2:15][Zn+])[CH3:12]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([CH2:15][C:14]([O:13][CH2:11][CH3:12])=[O:17])[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 2

HCID 140623094-Bromo-2-methoxypyridineHCID 178472538HCID 178472538, compound

Product 1

HCID 81850339Ethyl 2-(2-methoxypyridin-4-yl)acetateYield 38.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Combined 4-bromo-2-methoxypyridine (654 μl, 5.32 mmol), (2-ethoxy-2-oxoethyl)zinc(II) bromide (5850 μl, 5.85 mmol), and Pd(PPh3)4 catalyst (615 mg, 0.532 mmol) in THF (15.2 mL) and heated to 120° C. in a microwave for 5 minutes. The reaction was filtered through a course glass frit, concentrated to an oil and purified via flash chromatography (100 g silica gel using a 5% to 50% EtOAc in heptane gradient). The appropriate fractions were combined and concentrated to acquire ethyl 2-(2-methoxypyridin-4-yl)acetate (400 mg, 38.5% yield) as a colorless oil. MS m/z [M+H]+ 196.1.

Workup

  1. filtrationThe reaction was filtered through a course glass frit
  2. concentrationconcentrated to an oil
  3. custompurified via flash chromatography (100 g silica gel using a 5% to 50% EtOAc in heptane gradient)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-acf57fbf242e4755a2e2909d727810dd
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

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