Ammonium Chloride → 4-(1-Hydroxybutyl)-7-methoxy-2-trifluoromethyl-pyrazolo[1,5-a]pyridine
Reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[C:6]2[C:7]([CH:13]=[O:14])=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[N:5]2[N:4]=1.[CH2:18]([Mg]Br)[CH2:19][CH3:20].O1CCCC1.[Cl-].[NH4+]>O1CCCC1>[OH:14][CH:13]([C:7]1[C:6]2[N:5]([N:4]=[C:3]([C:2]([F:1])([F:16])[F:17])[CH:15]=2)[C:10]([O:11][CH3:12])=[CH:9][CH:8]=1)[CH2:18][CH2:19][CH3:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
The compound of Example 115 (300 mg) was dissolved in tetrahydrofuran (12.0 mL) in an argon atmosphere. While this solution was kept at −78° C., 1.04 mol/L n-propyl magnesium bromide/tetrahydrofuran solution (1.40 mL) was added dropwise and the mixture was stirred for 3 hours as it was allowed to gradually warm to −40° C. Subsequently, a saturated aqueous solution of ammonium chloride was added and the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent and subsequent purification of the residue by silica gel column chromatography (hexane:ethyl acetate=1:1) afforded the title compound as a yellow oil (265 mg).
Workup
- customwas kept at −78° C.
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed sequentially with water and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customEvaporation of the solvent and subsequent purification of the residue by silica gel column chromatography (hexane:ethyl acetate=1:1)
Sources & evidence
- ORD record
- ord-562e649230ef44d48b6ab6e2f3cb7473
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763617B2
Reaction notes
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