2-Bromo-3-methoxypyridine → 2-(1-Ethoxy-vinyl)-3-methoxy-pyridine

HRID 551759Notes

Reaction equation

HRID 551759 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C([Sn](CCCC)(CCCC)[C:15]([O:17][CH2:18][CH3:19])=[CH2:16])CCC>[Cu]I.CN(C=O)C>[CH2:18]([O:17][C:15]([C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1)=[CH2:16])[CH3:19]

Participants

5

Reactant 2

HCID 903642-Bromo-3-methoxypyridineHCID 619414Stannane, tributyl(1-ethoxyethenyl)-

Product 1

HCID 671711472-(1-Ethoxy-vinyl)-3-methoxy-pyridineYield 84.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Add copper (I) iodide (38 mg, 0.2 mmol) to a mixture of 2-bromo-3-methoxy-pyridine (188 mg, 1.0 mmol), tributyl(1-ethoxyvinyl)tin (0.68 mL, 2.0 mmol), and DMF (anhydrous, 4 mL) in a sealed tube. Flush with N2, seal, heat at 80° C. for 3 h. Purify the mixture by flash chromatography on silica gel eluting with 0-30% EtOAc/hexanes to afford 2-(1-ethoxy-vinyl)-3-methoxy-pyridine (151 mg, 84%).

Workup

  1. customFlush with N2
  2. customseal
  3. customPurify the mixture by flash chromatography on silica gel eluting with 0-30% EtOAc/hexanes

Sources & evidence

ORD record
ord-3d8d150c632d4673a761b425d36cecaa
Source dataset
uspto-grants-2011_05
Patent number
US07947841B2

Reaction notes

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