Sodium borohydride → HCID 68277844, compound
Reaction equation
[F:1][C:2]1[C:3]([CH:9]=[O:10])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].[BH4-].[Na+]>CO>[F:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-fluoro-4-methyl-2-pyridinecarbaldehyde (ASYMCHEM, 250 mg, 1.797 mmol) was dissolved under N2 atmosphere, in dry MeOH (5 mL). NaBH4 (ALDRICH, 187 mg, 4.94 mmol) was added. After 2 h reaction was completed. Solvent was evaporated. Residue was dissolved in ethyl acetate and partitioned between NaHCO3 aqueous saturated solution. Organic layer was dried over MgSO4 (anh), filtered and concentrated to obtain the title compound (200 mg, 1.42 mmol, 79%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 8.21-8.22 (m, 1H), 7.27-7.31 (m, 1H), 5.23 (t, 1H), 4.56 (dd, 2H), 2.27-2.28 (m, 3H). [ES+MS] m/z 142 (MH+).
Workup
- customAfter 2 h reaction
- customSolvent was evaporated
- dissolutionResidue was dissolved in ethyl acetate
- custompartitioned between NaHCO3 aqueous saturated solution
- dry with materialOrganic layer was dried over MgSO4 (anh)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-47ebc15c58fc46a5a6a9d58228e3eb3f
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08779153B2
Reaction notes
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