Ammonium Chloride → HCID 67389383, compound

HRID 1455222Notes

Reaction equation

HRID 1455222 reaction equation
C([Mg]Br)(C)C.I[C:7]1[CH:8]=[N:9][N:10]([C:12]2[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:11]=1.CON(C)[C:25](=[O:27])[CH3:26].[Cl-].[NH4+]>C1COCC1>[F:19][C:18]([F:21])([F:20])[C:17]1[C:12]([N:10]2[CH:11]=[C:7]([C:25](=[O:27])[CH3:26])[CH:8]=[N:9]2)=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 537505N-Methoxy-N-methylacetamideHCID 64428749HCID 64428749, compoundHCID 178418365HCID 178418365, compound

Product 1

HCID 67389383HCID 67389383, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Isopropylmagnesium bromide (2.0M in Et2O, 1.11 ml, 2.22 mmol) was added slowly to a solution of 2-(4-iodo-pyrazol-1-yl)-3-trifluoromethyl-pyridine (627 mg, 1.85 mmol) in 3 mL anhydrous THF at 0° C. under nitrogen. The reaction mixture was stirred at the same temperature for 2 hrs, and then followed by the addition of N-methoxy-N-methyl-acetamide (286 mg, 2.78 mmol). The mixture was allowed to warm to ambient temperature overnight. Saturated ammonium chloride was added to quench the reaction. Two layers were separated and the aqueous layer was extracted with ethyl acetate. The combined extract was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (25% EtOAC/Hexane) to give 1-[1-(3-trifluoromethyl-pyridin-2-yl)-1H-pyrazol-4-yl]-ethanone as a white solid (277 mg, 59% yield). 1H-NMR (400 MHz, CDCl3): δ 2.53 (s, 3H), 7.57 (dd, 1H, J=5.05, J=8.08), 8.18 (s, 1H), 8.27 (dd, 1H, J=1.52, J=8.08), 8.65 (s, 1H), 8.73 (d, 1H, J=4.03).

Workup

  1. customto quench
  2. customthe reaction
  3. customTwo layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. extractionThe combined extract
  6. washwas washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography on silica gel (25% EtOAC/Hexane)

Sources & evidence

ORD record
ord-57395d76dadf4a37ab493190377316a3
Source dataset
uspto-grants-2009_01
Patent number
US07482366B2

Reaction notes

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