Nitrogen → 4-(2-Methyl-[1,3]dioxolan-2-yl)-pyridine-2-carbaldehyde
Reaction equation
N#N.Br[C:4]1[CH:9]=[C:8]([C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)[CH:7]=[CH:6][N:5]=1.[Li]CCCC.CN([CH:24]=[O:25])C.[NH4+].[Cl-]>CCOCC>[CH3:15][C:10]1([C:8]2[CH:7]=[CH:6][N:5]=[C:4]([CH:24]=[O:25])[CH:9]=2)[O:14][CH2:13][CH2:12][O:11]1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 2-bromo-4-(2-methyl-[1,3]dioxolan-2-yl)-pyridine (1950 mg, 7.99 mmol) in dry Et2O (40 mL) was added n-BuLi (3.60 mL of a 2.5M solution in hexanes, 8.79 mmol) at −78° C. The reaction mixture was then stirred for 30 min at −78° C. before DMF (0.75 mL, 9.69 mmol) was added dropwise. The reaction mixture was allowed to warm up to rt and stirred at this temperature for 10 min. Sat. aq. NH4Cl (30 mL) was added, the layers separated and the aq. layer extracted with Et2O (3×30 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (10:1 to 2:1 hept-EA) gave the title compound as a pale yellow oil. TLC:rf (1:1 hept-EA)=0.40.
Workup
- additionwas added dropwise
- customthe layers separated
- extractionthe aq. layer extracted with Et2O (3×30 mL)
- dry with materialextracts were dried over Na2SO4
- filtrationfiltered
- customthe solvent was removed under reduced pressure
- customPurification of the residue by FC (10:1 to 2:1 hept-EA)
Sources & evidence
- ORD record
- ord-0e70b07222604c73b480959e2bb2a958
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536209B2
Reaction notes
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