Nitrogen → (2-Bromopyridin-4-yl)methanol

HRID 42801Notes

Reaction equation

HRID 42801 reaction equation
N#N.[Br:3][C:4]1[CH:9]=[C:8]([CH:10]=[O:11])[CH:7]=[CH:6][N:5]=1.[BH4-].[Na+].O>CO>[Br:3][C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 962WaterHCID 27629912-Bromo-4-pyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 14512957(2-Bromopyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), 2-bromo-pyridine-4-carbaldehyde (904 mg, 4.86 mmol) was dissolved in MeOH (10 mL). NaBH4 (236 mg, 5.99 mmol) was added portionwise at 0° C. and the reaction mixture stirred at rt for 1 h. Water (10 mL) was added and the mixture extracted with EA (3×20 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a white solid. TLC:rf (1:1 hept-EA)=0.22. LC-MS-conditions 02: tR=0.63 min; [M+H]+=188.33.

Workup

  1. extractionthe mixture extracted with EA (3×20 mL)
  2. dry with materialextracts were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-82d7cfcb2de64cdbb16efbaccd1a4360
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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