Water → Methyl 5-bromo-6-(cyclopropylmethoxy)picolinate

HRID 632143Notes

Reaction equation

HRID 632143 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]([OH:15])=[O:14])=[N:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1.IC.[C:18](=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C>[CH3:18][O:14][C:13]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[C:7]([O:8][CH2:9][CH:10]2[CH2:11][CH2:12]2)[N:6]=1)=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 710875435-Bromo-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

Product 1

HCID 71087286Methyl 5-bromo-6-(cyclopropylmethoxy)picolinateYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromo-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acid (Example 9 d, 0.4 g, 1.5 mmol), iodomethane (CAN 16519-98-5, 0.42 g, 3 mmol), sodium carbonate (0.16 g, 1.5 mmol) in DMF (10 mL) was stirred overnight at room temperature. Water was poured into the reaction solution and the resulting mixture was extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography (silica gel, 20 g, 5% ethyl acetate in petroleum ether) to yield the title compound (0.2 g, 0.7 mmol, 48%) as white solid; MS (EI): m/e=286.0 [M+H]+.

Workup

  1. customwas stirred overnight at room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate (3×30 mL)
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was purified by column chromatography (silica gel, 20 g, 5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-983252f5a99e4e5fa5c9ea38e8da3c46
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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