Methanol → (5-Bromo-3-fluoropyridin-2-yl)methanol
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([C:8](Cl)=[O:9])=[N:6][CH:7]=1.[BH4-].[Li+].CO>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([CH2:8][OH:9])=[N:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
5-Bromo-3-fluoropyridine-2-carbonyl chloride (0.50 g, 2.1 mmol) was dissolved in tetrahydrofuran (10 mL), cooled to 0° C. and treated with lithium borohydride (1.0 mL, 2 M tetrahydrofuran solution, 2.1 mmol, 1 equiv). After stirring for 30 minutes at 0° C., the mixture was treated with methanol (2 mL) and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate), providing the titled compound.
Workup
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate)
Sources & evidence
- ORD record
- ord-27632c39ac1f41b7a8c221daf11968e7
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895580B2
Reaction notes
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