Potassium Carbonate → 2-(Azetidin-1-yl)-6-bromopyridine

HRID 931114Notes

Reaction equation

HRID 931114 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[NH:16]1[CH2:19][CH2:18][CH2:17]1>CS(C)=O>[N:16]1([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=2)[CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122742,6-DibromopyridineHCID 12308726Azetidine hydrochloride

Product 1

HCID 573458512-(Azetidin-1-yl)-6-bromopyridineYield 33.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,6-dibromopyridine (100 mg, 0.424 mmol) in dimethylsulfoxide (5 mL) was added potassium carbonate (175.4 mg, 1.27 mmol) and azetidine hydrogen chloride (24.2 mg, 0.424 mmol) at room temperature. The reaction mixture was heated to 80° C. for 16 h, then was poured into ice cold water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, and concentrated under reduced pressure to afford 2-(azetidin-1-yl)-6-bromopyridine (30 mg)

Workup

  1. additionwas poured into ice cold water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-01275cf16836434b8b4071951a9f320d
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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