α-(4-Fluorophenyl)-3-(1-methylethyl)-1,2,4-triazolo[4,3-a]pyridine-6-methanol → HCID 10423205, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16]([CH:19]([CH3:21])[CH3:20])=[N:17][N:18]=3)[CH:15]=2)O)=[CH:4][CH:3]=1>[Zn].C(O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:10]2[CH:11]=[CH:12][C:13]3[N:14]([C:16]([CH:19]([CH3:20])[CH3:21])=[N:17][N:18]=3)[CH:15]=2)=[CH:4][CH:3]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 105 °C
Procedure
A mixture of (4-fluoro-phenyl)-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-methanol (591.3 mg, 2.07 mmol), Zn (1 g), and formic acid (3 mL) was heated at 105° C. for 4 days. The reaction was cooled, concentrated in vacuo, and quenched with saturated Na2CO3. The reaction mixture was extracted with ethyl acetate, the extracts dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (eluting with 10% methanol/ethyl acetate), followed by ethyl acetate precipitation (following addition of HCl in dioxane). The crude precipitate was recrystallized from MeOH/EtOAc to give the title compound (175.6 mg, 21%).
Workup
- temperatureThe reaction was cooled
- concentrationconcentrated in vacuo
- customquenched with saturated Na2CO3
- extractionThe reaction mixture was extracted with ethyl acetate
- dry with materialthe extracts dried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography (eluting with 10% methanol/ethyl acetate)
- customfollowed by ethyl acetate precipitation (following addition of HCl in dioxane)
- customThe crude precipitate was recrystallized from MeOH/EtOAc
Sources & evidence
- ORD record
- ord-3413319203d24ac2a4cd4f2ef3eed67d
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07321040B2
Reaction notes
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