Potassium Iodide → HCID 178524770, compound

HRID 2384108Notes

Reaction equation

HRID 2384108 reaction equation
C[Si](Cl)(C)C.[I-].[K+].C[O:9][C:10]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=1>CC#N>[OH:9][C:10]1[C:18]([C:19]([F:21])([F:20])[F:22])=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 6397ChlorotrimethylsilaneHCID 596082846-Methoxy-5-(trifluoromethyl)nicotinic acid

Product 1

HCID 178524770HCID 178524770, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of TMSCl (0.75 mL, 5.88 mmol) in dry MeCN is added potassium iodide (0.98 g, 5.88 mmol). The crude is stirred at room temperature for 10 mins. To this crude is added a solution of 6-methoxy-5-(trifluoromethyl)nicotinic acid (1.3 g, 5.88 mmol) in MeCN (2 mL). The crude is stirred at 80 deg C. for 4 hrs and room temperature for overnight. The crude is concentrated and diluted in ether and 1 N HCl. The organic layer is washed with water, brine, dried over MgSO4, filtered and concentrated. The crude is purified via RP-HPLC (SunFire C18, H2O(0.1% TFA)/CH3CN) to give 6-hydroxy-5-(trifluoromethyl)nicotinic acid (377 mg). HPLC retention time=0.85 minutes (condition B); MS 208.0 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 8.34 (s, 2H).

Workup

  1. stirringThe crude is stirred at 80 deg C
  2. waitfor 4 hrs
  3. waitroom temperature for overnight
  4. concentrationThe crude is concentrated
  5. additiondiluted in ether
  6. washThe organic layer is washed with water, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude is purified via RP-HPLC (SunFire C18, H2O(0.1% TFA)/CH3CN)

Sources & evidence

ORD record
ord-3290b922db4e4b4cb9a9fd8a9b7fd5fe
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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