Methyl iodide → 3-Bromo-4-(1-methoxy-ethyl)-pyridine

HRID 1253950Notes

Reaction equation

HRID 1253950 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[CH:10]([OH:12])[CH3:11].I[CH3:14]>CN(C=O)C>[Br:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[CH:10]([O:12][CH3:14])[CH3:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 667978531-(3-Bromopyridin-4-yl)ethanol

Product 1

HCID 667980463-Bromo-4-(1-methoxy-ethyl)-pyridineYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 148 mg, 3.71 mmol) was added to a solution of 1-(3-bromopyridin-4-yl)ethanol (500 mg, 2.475 mmol) in DMF (12 mL) at 0° C. After 10 min, iodomethane (1.237 mL, 2.475 mmol) was added dropwise and the resulting mixture was stirred at room temperature for another 1 h. The reaction was quenched by water, and the mixture was extracted with ethyl acetate. The combined extracts were dried over anhydrous Na2SO4. After filtration and concentration, the residue was purified by flash column (ethyl acetate-heptane, v/v, 0-30%) to give 418 mg of the title compound. 1HNMR (CDCl3, 400.3 MHz) δ 1.42 (d, J=6.4 Hz, 3H), 3.30 (s, 3H), 4.64 (q. J=0.4 Hz, 1H), 7.58 (s, 1H), 8.56 (s, 1H), 8.70 9s, 1H).

Workup

  1. customThe reaction was quenched by water
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by flash column (ethyl acetate-heptane, v/v, 0-30%)

Sources & evidence

ORD record
ord-4b1d6c3d85e34588b10567dee6549172
Source dataset
uspto-grants-2013_06
Patent number
US08455522B2

Reaction notes

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