2,2,2-Trifluoroethanol → 5-Methyl-6-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid

HRID 927334

Reaction equation

HRID 927334 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:11].[F:12][C:13]([F:17])([F:16])[CH2:14][OH:15].N12CCCN=C1CCCCC2>>[CH3:11][C:3]1[CH:4]=[CH:5][C:6]([C:8]([OH:10])=[O:9])=[N:7][C:2]=1[O:15][CH2:14][C:13]([F:17])([F:16])[F:12]

Participants

4

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 183244376-Chloro-5-methylpyridine-2-carboxylic acid

Product 1

HCID 710875095-Methyl-6-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acidYield 72%

Conditions

Temperature
150 °C

Procedure

A mixture of 6-chloro-5-methyl-pyridine-2-carboxylic acid (CAN 1166828-13-2, 200 mg, 1.17 mmol), 2,2,2-trifluoroethanol (466 mg, 336 μl, 4.66 mmol) and 1,8-diazabicyclo(5.4.0)undec-7-ene (CAN 83329-50-4, 887 mg, 870 μl, 5.83 mmol) was shaken in a sealed tube for 2 days at 140° C. and subsequently for additional 5 days at 150° C. The brown solution was poured into 25 mL ice/0.1 N HCl and extracted with i-PrOAc (2×25 mL). The organic layers were washed with ice/brine (2×25 mL). The organic layers were dried over sodium sulfate and concentrated in vacuo to give the title compound (198 mg, 58%) as off-white solid containing traces of starting material, MS (EI): m/e=233.9 [M−H]−.

Workup

  1. extractionextracted with i-PrOAc (2×25 mL)
  2. washThe organic layers were washed with ice/brine (2×25 mL)
  3. dry with materialThe organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bcb4b3c8ab254cad89debe33c62cb4b7
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Linked notes

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