Azetidine → HCID 66665392, compound

HRID 1186805Notes

Reaction equation

HRID 1186805 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1Cl.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:15]1[CH2:18][CH2:17][CH2:16]1>COCCOC>[N:15]1([C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[Br:1])[CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 10422AzetidineHCID 10796Cesium carbonateHCID 8176963-Bromo-4-chloropyridine

Product 1

HCID 66665392HCID 66665392, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a 16×100 mm reaction tube under N2 was added, 3-bromo-4-chloropyridine (320 mg, 1.663 mmol), cesium carbonate (1.65 g, 5.06 mmol), and 1,2-dimethoxyethane (3 mL). The reaction mixture was flushed with nitrogen and then treated with azetidine (210 μL, 3.12 mmol). The reaction mixture was securely capped, stirred at room temperature for 5 min, then heated at 90° C. for 18 h. The reaction mixture was filtered through a small Celite plug by gravity, washed with dichloromethane (30 mL) and the volatiles were evaporated in vacuo to give 350 mg (99%) of the title compound as a pale yellow solid.

Workup

  1. customTo a 16×100 mm reaction tube under N2
  2. additionwas added
  3. customThe reaction mixture was flushed with nitrogen
  4. customThe reaction mixture was securely capped
  5. temperatureheated at 90° C. for 18 h
  6. filtrationThe reaction mixture was filtered through a small Celite plug by gravity
  7. washwashed with dichloromethane (30 mL)
  8. customthe volatiles were evaporated in vacuo

Sources & evidence

ORD record
ord-3338643cfd304841a4c58af5ac9c9be6
Source dataset
uspto-grants-2014_03
Patent number
US08673922B2

Reaction notes

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