Ammonium Chloride → HCID 90009117, compound

HRID 531250Notes

Reaction equation

HRID 531250 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21]1[N:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[CH:23][CH:22]=1.[F:30][C:31]([Si](C)(C)C)([F:33])[F:32].[NH4+].[Cl-]>C(OCC)(=O)C.C1COCC1>[F:30][C:31]([F:33])([F:32])[C:27]([C:24]1[CH:25]=[N:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=1)([OH:29])[CH3:28]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 105348375-Acetyl-2-methoxypyridine

Product 1

HCID 90009117HCID 90009117, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

1.0M Tetra-butyl ammonium fluoride in THF (13.23 mL, 13.23 mmol) was added to a THF solution (20 mL) of 1-(6-methoxypyridin-3-yl)ethanone (2 g, 13.23 mmol) and (trifluoromethyl)trimethylsilane (3.76 g, 26.5 mmol) under nitrogen at 0° C. The reaction was warmed to 25° C. and stirred for 18 hours, at which time LCMS showed >95% conversion to product. The reaction was diluted with 50 mL ethyl acetate and poured into 100 mL saturated NH4Cl; the organic layer was washed with 100 mL brine, dried over sodium sulfate, filtered and the filtrate concentrated. Silica gel chromatography using a linear gradient of 0-100% ethyl acetate/hexanes gave the title compound as a white solid. LCMS (M+H)+: 222.0. 1H NMR (500 MHz, CDCl3): δ 8.36 (d, J=1.9 Hz, 1H), 7.81 (dd, J=1.9 and 8.8 Hz, 1H), 6.79 (d, J=8.8 Hz, 1H), 3.97 (s, 3H), 2.80 (s, 1H), 1.80 (s, 3H).

Workup

  1. washthe organic layer was washed with 100 mL brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-1e5c3e5036f741a2aef4243dd9c8bfb1
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

Loading…