Dimethylformamide → HCID 89853000, compound

HRID 931115Notes

Reaction equation

HRID 931115 reaction equation
C([Li])CCC.[N:6]1([C:10]2[CH:15]=[CH:14][CH:13]=[C:12](Br)[N:11]=2)[CH2:9][CH2:8][CH2:7]1.CN(C)[CH:19]=[O:20]>O1CCCC1>[N:6]1([C:10]2[N:11]=[C:12]([CH:19]=[O:20])[CH:13]=[CH:14][CH:15]=2)[CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 573458512-(Azetidin-1-yl)-6-bromopyridineHCID 178418339Butyllithium

Product 1

HCID 89853000HCID 89853000, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of n-butyllithium in hexanes (0.3 g, 4.69 mmol) was added dropwise to a solution of 2-(azetidin-1-yl)-6-bromopyridine (0.5 g, 2.34 mmol) in dry tetrahydrofuran (20 mL) at −78° C. After stirring for 30 min at −78° C., N,N-dimethylformamide (0.34 g, 4.69 mmol) was added. The reaction mixture was stirred for 3 h at −78° C., then the reaction mixture was quenched with an aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via flash chromatography (60-120 mesh silica; 4-5% ethyl acetate in petroleum ether, twice) to afford 6-(azetidin-1-yl)picolinaldehyde (0.2 g, 43%). MS (ES+) (M+H) 163.1380; LCMS retention time: 5.59 minutes (Method X).

Workup

  1. stirringThe reaction mixture was stirred for 3 h at −78° C.
  2. customthe reaction mixture was quenched with an aqueous ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified via flash chromatography (60-120 mesh silica

Sources & evidence

ORD record
ord-a9b7a6f04b994a73b231a344d87097f1
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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