Methanol → (5-Bromo-6-(2,4-difluorophenoxy)pyridin-3-yl)methanol
Reaction equation
[Br:1][C:2]1[C:3]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].CO>O1CCCC1>[Br:1][C:2]1[CH:10]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][C:3]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
The product from Example 311a (1.0 g, 3.03 mmol) and borane tetrahydrofuran complex (6.06 mL, 6.06 mmol) were combined in tetrahydrofuran (15.15 mL) and heated at 50° C. for 2 hours, cooled, treated with 10 mL of methanol, heated at 50° C. for 1 hour, cooled and concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (Na2SO4), filtered, and concentrated. Purification by chromatography (silica gel, 0-50% ethyl acetate in heptanes) afforded the title compound (0.73 g, 76%).
Workup
- temperaturecooled
- temperatureheated at 50° C. for 1 hour
- temperaturecooled
- concentrationconcentrated
- customThe residue was partitioned between ethyl acetate and water
- washThe organic layer was washed with saturated aqueous sodium chloride
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customPurification by chromatography (silica gel, 0-50% ethyl acetate in heptanes)
Sources & evidence
- ORD record
- ord-e9d620f55da54434a8eef52e24f05f50
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296741B2
Reaction notes
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