5-Bromo-3-pyridinecarboxaldehyde → (5-Bromo-pyridin-3-yl)-cyclopropyl-methanol

HRID 1623515Notes

Reaction equation

HRID 1623515 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:8]=[O:9])[CH:7]=1.[CH:10]1([Mg]Br)[CH2:12][CH2:11]1>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH:10]2[CH2:12][CH2:11]2)[OH:9])[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 178418630HCID 178418630, compound2×

Product 1

HCID 59825022(5-Bromo-pyridin-3-yl)-cyclopropyl-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-5-pyridinecarboxaldehyde (651 mg, 3.50 mmol) in THF (20 ml) at −78° C. was added cyclopropylmagnesium bromide (0.5M in THF, 7.49 ml, 3.74 mmol). After 10 minutes, additional cyclopropylmagnesium bromide (0.5M THF, 3.0 mL, 1.5 mmol) was added. After stirring for an additional five minutes the reaction was quenched with saturated aqueous ammonium chloride. The resulting mixture was diluted with dichloromethane and water and the layers were separated. The aqueous layer was extracted two additional times with dichloromethane, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane, 0 to 7%) to afford (5-bromo-pyridin-3-yl)-cyclopropyl-methanol; MS (ES+) m/z 228.2 (M+H)+.

Workup

  1. customwas quenched with saturated aqueous ammonium chloride
  2. additionThe resulting mixture was diluted with dichloromethane and water
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted two additional times with dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane, 0 to 7%)

Sources & evidence

ORD record
ord-a36ff90377cb4bc595d12fed403943f4
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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