Sodium borohydride → 5-(Hydroxymethyl)-N,N-dimethylfuro[2,3-b]pyridine-2-carboxamide

HRID 931385Notes

Reaction equation

HRID 931385 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[O:11][C:8]2=[N:9][CH:10]=1)=[O:4]>CO.C1COCC1>[OH:4][CH2:3][C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[O:11][C:8]2=[N:9][CH:10]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 900505435-Formyl-N,N-dimethylfuro[2,3-b]pyridine-2-carboxamide

Product 1

HCID 1180232315-(Hydroxymethyl)-N,N-dimethylfuro[2,3-b]pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

Sodium borohydride (6.0 g, 0.16 mol) was added to a solution of 5-formyl-N,N-dimethylfuro[2,3-b]pyridine-2-carboxamide (6.9 g, 0.032 mol) in methanol (80 mL) and THF (20 mL) at 0° C., and the resulting mixture was gradually warmed to 23° C. and stirred for 1 h. The excess of sodium borohydride was carefully quenched with water. The reaction mixture was concentrated, and then extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 70% ethyl acetate in petroleum ether to give the title compound. MS: m/z=221.0 (M+1).

Workup

  1. customThe excess of sodium borohydride was carefully quenched with water
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel eluting with 70% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-1928ae1d056e42309fcd7a265dbf6949
Source dataset
uspto-grants-2016_03
Patent number
US09296750B2

Reaction notes

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