Hydrochloric Acid → HCID 12009735, compound

HRID 1007069Notes

Reaction equation

HRID 1007069 reaction equation
[CH3:1][N:2]1[C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH:15][CH:16]=O)[N:9]=2)=[CH:5][C:4]([C:18]([F:21])([F:20])[F:19])=[N:3]1.Cl>C1COCC1>[CH3:1][N:2]1[C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH:15][CH3:16])[N:9]=2)=[CH:5][C:4]([C:18]([F:21])([F:20])[F:19])=[N:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12010723HCID 12010723, compound

Product 1

HCID 12009735HCID 12009735, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

4.40 g (14.7 mmol) of 2-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-6-(formylaminomethyl)-pyridine were dissolvej in 45 ml of anhydrous THF under an inert gas atmosphere and at 0° C. 4.17 ml (44.0 mmol) of borane dimethylsulfide complex were added to the solution. The mixture was heated at 50° C. for 2.5 h. After cooling to room temperature, the reaction solution was admixed with 100 ml of 2 N HCl, stirred for 1 h and then extracted with ethyl acetate. The aqueous phase was rendered alkaline with 2 N NaOH and subjected to repeated extraction with ethyl acetate. The extracts were dried over MgSO4 and concentrated to dryness.

Workup

  1. addition4.17 ml (44.0 mmol) of borane dimethylsulfide complex were added to the solution
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with ethyl acetate
  4. extractionextraction with ethyl acetate
  5. dry with materialThe extracts were dried over MgSO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-49e99182fea2416991838b0cb57f02c8
Source dataset
uspto-grants-2004_09
Patent number
US06794336B2

Reaction notes

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