2-Chloro-5-hydroxypyridine → HCID 86642879, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].F[C:16]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]>CC1CCCO1.CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:16]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:17]=2[C:18]([O:20][CH3:21])=[O:19])=[CH:4][CH:3]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 6-chloropyridin-3-ol (2.41 g) in 2-methyltetrahydrofuran (20 mL) and N,N-dimethylformamide (4 mL) was added potassium tert-butoxide (1.0M in tetrahydrofuran) (18.60 mL). The reaction was stirred for 15 minutes, then methyl 2,4-difluorobenzoate (3.52 g) was added as a solution in 2-methyltetrahydrofuran (2 mL). The reaction was then heated to 80° C. and stirred under a nitrogen atmosphere for 3 days. The reaction was cooled, diluted with ethyl acetate (100 mL), washed with water (50 mL), 1N aqueous HCl (50 mL), and brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Reveleris 80 g), eluting with 10% ethyl acetate/hexanes provided the title compound.
Workup
- stirringstirred under a nitrogen atmosphere for 3 days
- temperatureThe reaction was cooled
- washwashed with water (50 mL), 1N aqueous HCl (50 mL), and brine (50 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- washSilica gel chromatography (Reveleris 80 g), eluting with 10% ethyl acetate/hexanes
Sources & evidence
- ORD record
- ord-4ad5465ef1eb47309d3a81207ae6e793
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029404B2
Reaction notes
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