Methyl iodide → 5-Bromo-3-isopropoxy-2-methoxymethyl-pyridine

HRID 445739Notes

Reaction equation

HRID 445739 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH:11]([CH3:13])[CH3:12])[C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.[H-].[Na+].I[CH3:17]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH:11]([CH3:13])[CH3:12])[C:5]([CH2:8][O:9][CH3:17])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59612931(5-Bromo-3-isopropoxy-pyridin-2-yl)-methanol

Product 1

HCID 596131045-Bromo-3-isopropoxy-2-methoxymethyl-pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (5-bromo-3-isopropoxy-pyridin-2-yl)-methanol (stage 190.1.2, 0.61 mmol) in DMF (3 ml) was added 55% NaH in oil (0.688 mmol) was added. The RM was stirred for 30 min at rt then was added iodomethane (0.684 mmol). The RM was stirred for 2.5 h at rt then was quenched with MeOH and purified by preparative HPLC. The fractions containing product were combined, basified with NaHCO3, concentrated and extracted with dichloromethane (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give the title compound as a yellow oil. (HPLC: tR 2.83 min (Method A); M+H=260, 262 MS-ES).

Workup

  1. additionwas added
  2. stirringThe RM was stirred for 2.5 h at rt
  3. customthen was quenched with MeOH
  4. custompurified by preparative HPLC
  5. additionThe fractions containing product
  6. concentrationconcentrated
  7. extractionextracted with dichloromethane (2×)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-f37e50aacb174dbc84dd88772b9072ba
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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