Sodium borohydride → HCID 68277844, compound

HRID 1467903Notes

Reaction equation

HRID 1467903 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

HCID 4311764Sodium borohydrideHCID 447548763-Fluoro-4-methylpyridine-2-carbaldehyde

Product 1

HCID 68277844HCID 68277844, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. customAfter 2 h reaction
  2. customSolvent was evaporated
  3. dissolutionResidue was dissolved in ethyl acetate
  4. custompartitioned between NaHCO3 aqueous saturated solution
  5. dry with materialOrganic layer was dried over MgSO4 (anh)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-178c1e5b4cbd47ab9c42d10edbeddcb2
Source dataset
uspto-grants-2015_04
Patent number
US09000181B2

Reaction notes

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