Ammonium Chloride → HCID 68157595, compound

HRID 243193Notes

Reaction equation

HRID 243193 reaction equation
CC(C)([O-])C.[K+].[CH3:7][N:8]1[C:12]([NH2:13])=[CH:11][CH:10]=[N:9]1.F[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23].[Cl-].[NH4+]>C1COCC1>[F:21][C:19]1[CH:18]=[CH:17][C:16]([N+:22]([O-:24])=[O:23])=[C:15]([NH:13][C:12]2[N:8]([CH3:7])[N:9]=[CH:10][CH:11]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 679672,4-DifluoronitrobenzeneHCID 1369272-Methyl-2H-pyrazol-3-ylamineHCID 23665647Potassium tert-butoxide

Product 1

HCID 68157595HCID 68157595, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium tert-butoxide (1.16 g, 10.3 mmol) was added to a solution of 2-methyl-2H-pyrazol-3-ylamine (0.50 g, 5.15 mmol) in THF (10 mL) at 0° C. under nitrogen and the resultant mixture stirred for 15 min. 2,4-difluoro-1-nitrobenzene (0.98 g, 6.18 mmol) in THF (5 mL) was added and stirring continued for 2 h. The reaction mixture was poured into saturated aqueous ammonium chloride solution and extracted with EtOAc (×3). The combined EtOAc extracts were dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by chromatography (SiO2, 0-2% methanol in DCM) to give the title compound as a yellow/brown crystalline solid (0.98 g, 80%). LCMS (Method C): RT 2.98 min [M+H]+ 237.0

Workup

  1. extractionextracted with EtOAc (×3)
  2. dry with materialThe combined EtOAc extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was purified by chromatography (SiO2, 0-2% methanol in DCM)

Sources & evidence

ORD record
ord-e912b7a959664847af29bdd9a0174a5e
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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