Sodium borohydride → HCID 57537637, compound

HRID 886627Notes

Reaction equation

HRID 886627 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[C:9]([C:10](=[O:16])[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[CH:8][C:7]([Br:17])=[CH:6][N:5]=1>CO>[NH2:3][C:4]1[C:9]([CH:10]([OH:16])[C:11]([N:13]([CH3:14])[CH3:15])=[O:12])=[CH:8][C:7]([Br:17])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57537502HCID 57537502, compound

Product 1

HCID 57537637HCID 57537637, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium borohydride (85.5 mg, 2.25 mmol) was added to methanol (5 mL) at 0° C. After 5 min., 2-(2-amino-5-bromo-pyridin-3-yl)-N,N-dimethyl-2-oxo-acetamide (408 mg, 1.50 mmol) in MeOH (15 mL) was added. After 1 h, the reaction was quenched by addition of saturated NH4Cl and the mixture was concentrated in vacuo. The residue was extracted with ethyl acetate, dried over Na2SO4 and purified by silica gel chromatography using DCM and MeOH to afford 2-(2-amino-5-bromo-pyridin-3-yl)-2-hydroxy-N,N-dimethyl-acetamide (234 mg, 57.1%) as a brown oily solid. The material was used in the next step. MS: m/z 274 (M+H+).

Workup

  1. waitAfter 1 h
  2. customthe reaction was quenched by addition of saturated NH4Cl
  3. concentrationthe mixture was concentrated in vacuo
  4. extractionThe residue was extracted with ethyl acetate
  5. dry with materialdried over Na2SO4
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-6b074749ed1a46eab519f8a9d6ed600f
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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