Ammonium Chloride → HCID 71293874, compound

HRID 1747538Notes

Reaction equation

HRID 1747538 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([CH:13]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][N:8]=1.CON(C)[C:29](=[O:31])[CH3:30].[Cl-].[NH4+]>C1(C)C=CC=CC=1.O.C1COCC1>[Si:19]([O:18][CH:13]([C:11]1[CH:10]=[CH:9][N:8]=[C:7]([C:29](=[O:31])[CH3:30])[CH:12]=1)[C:14]([F:17])([F:16])[F:15])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 537505N-Methoxy-N-methylacetamideHCID 86678193HCID 86678193, compoundHCID 178418339Butyllithium

Product 1

HCID 71293874HCID 71293874, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To toluene (9 mL) were added dropwise at −78° C. n-butyllithium (2.66 mol/L solution in n-hexane, 1.12 mL, 2.97 mmol) and a solution of 2-bromo-4-(1-(tert-butyldimethylsilyloxy)-2,2,2-trifluoroethyl)pyridine (1.00 g, 2.70 mmol) obtained in Step 2 in toluene (3.0 mL), and the mixture was stirred at the same temperature for 30 minutes. THF (3.0 mL) was added to the resulting solution and the mixture was stirred at −78° C. for 30 minutes. N-methoxy-N-methylacetamide (1.38 mL, 13.5 mmol) was added and the mixture was stirred for 2 hours allowing the temperature to rise slowly to room temperature. A saturated aqueous ammonium chloride solution and water were added to the reaction mixture. Extraction with ethyl acetate and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give 1-(4-(1-(tert-butyldimethylsilyloxy)-2,2,2-trifluoroethyl)pyridin-2-yl)ethanone (645 mg, 72% yield).

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. customto rise slowly to room temperature
  3. extractionExtraction with ethyl acetate
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent in the filtrate was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-2290638b41614081b056097c2a53aa19
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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