Methanol → HCID 86730205, compound
Reaction equation
[Cl:1][C:2]1[C:3]([C:13]([F:16])([F:15])[CH3:14])=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7](OCC)=[O:8].[Li+].[BH4-].CO>CCOCC>[Cl:1][C:2]1[CH:12]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][C:3]=1[C:13]([F:15])([F:16])[CH3:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a solution of ethyl 5-chloro-6-(1,1-difluoroethyl)nicotinate (2.68 g, 10.74 mmol) in Et2O (40 mL) was added LiBH4 (0.351 g, 16.10 mmol), followed by dropwise addition of methanol (0.653 mL, 16.10 mmol). The reaction was refluxed at 40° C. for one hour. The reaction mixture was then cooled to 0° C., and quenched with HCl (1M) until pH=2 for aqueous layer. The phases were separated and the aqueous layer was extracted with DCM (3×50 mL). The organic was then dried (Na2SO4) and concentrated under reduced pressure to give final crude product (2.12 g). LCMS m/z 208.0 (M+H)+, Rt 0.63 min.
Workup
- temperatureThe reaction mixture was then cooled to 0° C.
- customquenched with HCl (1M) until pH=2 for aqueous layer
- customThe phases were separated
- extractionthe aqueous layer was extracted with DCM (3×50 mL)
- dry with materialThe organic was then dried (Na2SO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-3da3d730e6284df293efac5cc9349a8c
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957068B2
Reaction notes
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