Potassium Carbonate → Methyl 5-(but-2-yn-1-yloxy)picolinate

HRID 1950771Notes

Reaction equation

HRID 1950771 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][N:6]=1)=[O:4].Br[CH2:13][C:14]#[C:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:13][C:14]#[C:15][CH3:16])=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 4715126Methyl 5-hydroxypyridine-2-carboxylate

Product 1

HCID 58449213Methyl 5-(but-2-yn-1-yloxy)picolinateYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-hydroxy-pyridine-2-carboxylic acid methyl ester (271 mg) and 1-bromo-2-butine (283 mg) in DMF (5 ml) was treated with potassium carbonate (367 mg) and heated to 100° C. for 16 h. the mixture was partitioned between water and ethyl acetate, the organic layer was dried, evaporated and the residue was purified by chromatography using heptane/ethyl acetate (gradient from 0-80% ethyl acetate) to give the title product (266 mg) as a pale yellow solid. MS: m/z=206.1 [M+H]+.

Workup

  1. customwas partitioned between water and ethyl acetate
  2. customthe organic layer was dried
  3. customevaporated
  4. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-535408dc90c546b58a0049c7be7a6af1
Source dataset
uspto-grants-2013_03
Patent number
US08404680B2

Reaction notes

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