Benzyl Alcohol → 3-Benzyloxy-1-(7-methoxy-2-trifluoromethyl-pyrazolo[1,5-a]pyridine-4-yl)-propane-1-one
Reaction equation
[CH3:1][O:2][C:3]1[N:8]2[N:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=[C:7]2[C:6]([C:16](=[O:19])[CH2:17][CH3:18])=[CH:5][CH:4]=1.[CH2:20]([OH:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl>[CH2:20]([O:27][CH2:18][CH2:17][C:16]([C:6]1[C:7]2[N:8]([N:9]=[C:10]([C:12]([F:15])([F:13])[F:14])[CH:11]=2)[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:19])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Participants
4
Procedure
A solution of the compound of Example 319 (3.42 g) and benzyl alcohol (1.37 g) in dichloromethane (50 mL) was added to dichloro bis(acetonitrile) palladium (II) (329 mg) in a stream of argon gas. The mixture was stirred at room temperature overnight, followed by addition of benzyl alcohol (500 mL) and stirring overnight. The insoluble material was removed by filtration through Celite. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2). The product was further purified by amino-silica gel column chromatography (hexane:ethyl acetate=3:2) to afford the title compound as a pale yellow powder (2.47 g).
Workup
- stirringstirring overnight
- customThe insoluble material was removed by filtration through Celite
- customThe solvent was evaporated
- customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2)
- customThe product was further purified by amino-silica gel column chromatography (hexane:ethyl acetate=3:2)
Sources & evidence
- ORD record
- ord-beb82b0a1285494388793e6d60fd6f56
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763617B2
Reaction notes
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