Sodium borohydride → HCID 57895156, compound

HRID 39449Notes

Reaction equation

HRID 39449 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[O:9])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[OH:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57895127HCID 57895127, compound

Product 1

HCID 57895156HCID 57895156, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (6-amino-pyridin-3-yl)-(2-methoxy-phenyl)-methanone (14 g, 61.4 mol) in CH3OH (150 mL) was added NaBH4 (3.48 g, 92.1 mmol) portion-wise at 0° C. After the addition was completed, the reaction was warmed to room temperature and stirred at room temperature for 1 hr. The solvent was removed in vacuo and water (100 mL) was added to the residue. The mixture was extracted with dichloromethane (100 mL×3). The combined organic layers were washed with saturated solution of NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo to give a crude product that was used directly in the next step with no further purification.

Workup

  1. additionAfter the addition
  2. customThe solvent was removed in vacuo and water (100 mL)
  3. additionwas added to the residue
  4. extractionThe mixture was extracted with dichloromethane (100 mL×3)
  5. washThe combined organic layers were washed with saturated solution of NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43e0223dda3d4b59b4cd0a2488a8f31a
Source dataset
uspto-grants-2013_09
Patent number
US08524910B2

Reaction notes

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