Phosphorus oxychloride → HCID 59134895, compound

HRID 1993766Notes

Reaction equation

HRID 1993766 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:12])=[CH:8][C:9]=2O)[C:4]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:23]=[CH:22][CH:21]=[N:20]3)=[CH:15][C:14]=2[CH3:24])=[N:3]1.P(Cl)(Cl)([Cl:27])=O>C(#N)C>[Cl:27][C:9]1[CH:8]=[C:7]([CH3:12])[N:6]=[C:5]2[C:4]([C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH:23]=[CH:22][CH:21]=[N:20]4)=[CH:15][C:14]=3[CH3:24])=[N:3][N:2]([CH3:1])[C:10]=12

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178428860HCID 178428860, compound

Product 1

HCID 59134895HCID 59134895, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of compound 3e (1.0 g) in anhydrous acetonitrile (10 mL) was added phosphorous oxychloride (0.60 mL). The reaction was refluxed under nitrogen for 2 hours. The reaction mixture was cooled and quenched on ice with H20. The mixture was basified to pH 8 with sodium bicarbonate. The product was extracted with ethyl acetate (3×50 mL). The organic layers were combined, dried over magnesium sulfate and concentrated to afford 7-chloro-1,5-dimethyl-3-(2-methyl-4-pyrazol-1-yl-phenyl)-1H-pyrazolo[4,3-b]pyridine as a yellow oil. The compound was purified by silica gel chromatography, using 30% ethyl acetate/hexanes as eluent to provide 1.0 g (99%) of compound 4a as a white solid; LC/MS: [M+H]=338.2.

Workup

  1. temperatureThe reaction was refluxed under nitrogen for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. customquenched on ice with H20
  4. extractionThe product was extracted with ethyl acetate (3×50 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-44417f4d41ef4d4c9076ccd6048911ba
Source dataset
uspto-grants-2010_01
Patent number
US07652035B2

Reaction notes

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