Tetrahydrofuran → HCID 67974893, compound

HRID 468909Notes

Reaction equation

HRID 468909 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([Cl:10])[C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.O1CCCC1.[F:17][C:18]([Si](C)(C)C)([F:20])[F:19].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([Cl:10])[C:5]([CH:8]([OH:9])[C:18]([F:20])([F:19])[F:17])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 86674975HCID 86674975, compound

Product 1

HCID 67974893HCID 67974893, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromo-3-chloro-4-methyl-pyridine-2-carbaldehyde (123.9 mg; 0.5284 mmol) in tetrahydrofuran (5.0 mL; 62 mmol) at 0° C. was added (trifluoromethyl)trimethylsilane (0.170 mL; 1.1 mmol) followed by tetrabutylammonium fluoride (1 mol/L) in THF (1.6 mL; 1.6 mmol). The resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was then diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered, and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (12 g silica, solvent gradient: 0-50% ethyl acetate in heptanes) to yield 119.7 mg (74%) of the title compound. LCMS (ESI): M+H=304.0; 1H NMR (400 MHz, DMSO) δ 8.76 (s, 1H), 6.92 (d, J=6.9 Hz, 1H), 5.58 (p, J=6.9 Hz, 1H), 2.55 (s, 3H).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude product was purified via flash chromatography on silica gel (12 g silica, solvent gradient: 0-50% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-e72f20b35d764aaaa42640885836b498
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

Loading…