2-Bromopyridine → HCID 67979508, compound

HRID 528757Notes

Reaction equation

HRID 528757 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[C:13]([O:17][C:18]([N:20]1[CH2:23][CH:22]([CH:24]=[O:25])[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>CCOCC>[C:13]([O:17][C:18]([N:20]1[CH2:23][CH:22]([CH:24]([OH:25])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 10726182Tert-butyl 3-formylazetidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 67979508HCID 67979508, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

To 1.51 g (9.55 mmol) bromopyridine in 50 mL ether at −20° C. was added 6 mL (1.6 M in hexane, 9.6 mmol) n-butyl lithium, after 10 minutes the mixture was cooled to −78° C. and 1.61 g (8.7 mmol) 3-formyl-azetidine-1-carboxylic acid tert-butyl ester in 20 mL ether was added. The mixture was stirred and allowed to warm to room temperature, quenched with 50 mL 1 M sodium bicarbonate solution and then extracted with 50 mL DCM. The organic layer was dried over Na2SO4. After filtration and evaporation of the solvent the desired product was purified by column chromatography (silica, heptane/EtOAc 1:1 to EtOAc).

Workup

  1. temperatureto warm to room temperature
  2. customquenched with 50 mL 1 M sodium bicarbonate solution
  3. extractionextracted with 50 mL DCM
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationAfter filtration and evaporation of the solvent the desired product
  6. customwas purified by column chromatography (silica, heptane/EtOAc 1:1 to EtOAc)

Sources & evidence

ORD record
ord-4bce992c89684a5caac9563dac6b595a
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

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