3-Bromopyridine-4-carboxaldehyde → (3-Bromopyridin-4-yl)methanol

HRID 1405087Notes

Reaction equation

HRID 1405087 reaction equation
[Br:1][C:2]1[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 27629973-Bromopyridine-4-carboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 46840038(3-Bromopyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cold solution of 3-bromoisonicotinaldehyde (2.5 g, 13.44 mmol) in MeOH (Volume: 100 ml) was added sodium borohydride (1.017 g, 26.9 mmol) and the reaction mixture was stirred at that temperature for 1 hour. The reaction mixture was then quenched with satd. NaHCO3, filtered, and evaporated to remove MeOH. The aqueous layer was extracted with EtOAc (2×). The combined organics were washed with satd. NaHCO3 and brine, dried, and concentrated to give Intermediate 65A as a white solid. MS (ES): m/z=189.9 [M+H]+.

Workup

  1. customThe reaction mixture was then quenched with satd
  2. filtrationNaHCO3, filtered
  3. customevaporated
  4. customto remove MeOH
  5. extractionThe aqueous layer was extracted with EtOAc (2×)
  6. washThe combined organics were washed with satd
  7. dry with materialNaHCO3 and brine, dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-036f6be1b37b431ebb68b0a03faa7796
Source dataset
uspto-grants-2014_12
Patent number
US08916553B2

Reaction notes

Loading…