4-Fluorophenylhydrazine hydrochloride → 4-[5-dimethoxymethyl-2-(4-fluoro-phenyl)-2H-pyrazol-3-yl]-pyridine

HRID 1454291Notes

Reaction equation

HRID 1454291 reaction equation
[CH3:1][O:2][CH:3]([O:15][CH3:16])[C:4](=O)[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)=O.Cl.[F:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][NH2:26])=[CH:21][CH:20]=1>C(O)C>[CH3:1][O:2][CH:3]([O:15][CH3:16])[C:4]1[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[N:25]([C:22]2[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=2)[N:26]=1

Participants

4

Reactant 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 178745444,4-Dimethoxy-1-pyridin-4-yl-butane-1,3-dione

Product 1

HCID 536347204-[5-dimethoxymethyl-2-(4-fluoro-phenyl)-2H-pyrazol-3-yl]-pyridineYield 9.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 4,4-dimethoxy-1-pyridin-4-yl-butane-1,3-dione (20 g, Reference Example 2) in ethanol (500 ml) was treated with 4-fluorophenylhydrazine hydrochloride (29 g). The mixture was refluxed for 0.5 hour then evaporated. The residual yellow oil was subjected to flash chromatography on silica eluting with a mixture of methanol and dichloromethane (99:1, v/v) to give the title compound as a brown oil (2.7 g). MS: 314 [MH]+. RF=0.27 (ethyl acetate, determined by thin layer chromatography on silica).

Workup

  1. temperatureThe mixture was refluxed for 0.5 hour
  2. customthen evaporated
  3. additionThe residual yellow oil was subjected to flash chromatography on silica eluting with a mixture of methanol and dichloromethane (99:1

Sources & evidence

ORD record
ord-49164f33f3c2420c8c7bea947d73d5e4
Source dataset
uspto-grants-2009_01
Patent number
US07479501B2

Reaction notes

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