Hydrochloric Acid → HCID 71294459, compound

HRID 469765Notes

Reaction equation

HRID 469765 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[I:11].[OH-].[K+].[F:14][C:15]([F:19])([F:18])[CH2:16][OH:17].Cl>CS(C)=O.O>[I:11][C:3]1[C:2]([O:17][CH2:16][C:15]([F:19])([F:18])[F:14])=[N:7][CH:6]=[C:5]([CH:4]=1)[C:8]([OH:10])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 14797Potassium HydroxideHCID 222714776-Chloro-5-iodonicotinic acid

Product 1

HCID 71294459HCID 71294459, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

6-Chloro-5-iodo-3-pyridinecarboxylic acid (CAN 59782-87-5, 4.7 g, 16.6 mmol) was dissolved in DMSO (49.5 ml). Potassium hydroxide pellets (2.79 g, 49.7 mmol) and 2,2,2-trifluoroethanol (2.16 g, 1.55 ml, 21.6 mmol) were added slowly at room temperature under argon. The reaction mixture was stirred for 2 h at rt; water (35 mL) was added and the mixture was cooled to 0-5° C. Concentrated HCl solution (8 mL) was added drop by drop and the precipitated solid was collected, washed with cold water and dried. The crude material was purified by flash chromatography (silica gel, 150 g, 0% to 20% i-propyl acetate in n-heptane +10% of acetic acid) to give the title compound (1.6 g, 28%) as colorless solid; MS (ESI) 345.7 (M−H)−.

Workup

  1. additionwere added slowly at room temperature under argon
  2. temperaturethe mixture was cooled to 0-5° C
  3. customthe precipitated solid was collected
  4. washwashed with cold water
  5. customdried
  6. customThe crude material was purified by flash chromatography (silica gel, 150 g, 0% to 20% i-propyl acetate in n-heptane +10% of acetic acid)

Sources & evidence

ORD record
ord-8097bc92a97f49f69e7289b0a572d7ee
Source dataset
uspto-grants-2014_01
Patent number
US08629166B2

Reaction notes

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