Acetic Acid → HCID 21904679, compound

HRID 1246632Notes

Reaction equation

HRID 1246632 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:12][C:13]([F:23])([F:22])[O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].C(O)(=O)C>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][C:13]([F:12])([F:22])[F:23])=[CH:16][CH:17]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 70015p-(Trifluoromethoxy)phenolHCID 27633425-Bromo-2-chloronicotinic acid

Product 1

HCID 21904679HCID 21904679, compoundYield 24.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-bromo-2-chloronicotinic acid (2.36 g, 10 mmol), 4-trifluoromethoxyphenol (2.14 g, 12 mmol) and K2CO3 (4.14 g, 30 mmol) in DMF (30 mL) was heated at 140° C. for 24 h. After cooling to room temperature the mixture was diluted with water (150 mL) and the pH was adjusted to 6 with acetic acid. The mixture was extracted with EtOAc (3×50 mL) and the combined organic extracts were dried (MgSO4) and evaporated to give an oil. This was triturated with water to give a sticky solid which was filtered and washed with water and then pentane. The resulting beige solid was suspended in further pentane, sonicated, filtered and dried in vacuo at 60° C. to give the product (0.92 g, 24%) as a beige solid; (δH (CDCl3, 300 MHz) 7.19 (2H, m), 7.28 (2H, m), 8.35 (1H, s), 8.58 (1H, s); MS m/z (TS+) 378, 380 (MH+).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionThe mixture was extracted with EtOAc (3×50 mL)
  3. dry with materialthe combined organic extracts were dried (MgSO4)
  4. customevaporated
  5. customto give an oil
  6. customThis was triturated with water
  7. customto give a sticky solid which
  8. filtrationwas filtered
  9. washwashed with water
  10. customsonicated
  11. filtrationfiltered
  12. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-87667e1915834637895dd643ee891f51
Source dataset
uspto-grants-2006_10
Patent number
US07129234B2

Reaction notes

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