5-Bromo-6-chloropyridine-3-sulfonyl chloride → 5-(Azetidine-1-sulfonyl)-3-bromo-2-chloropyridine

HRID 1990140Notes

Reaction equation

HRID 1990140 reaction equation
Cl.[NH:2]1[CH2:5][CH2:4][CH2:3]1.[Br:6][C:7]1[C:8]([Cl:17])=[N:9][CH:10]=[C:11]([S:13](Cl)(=[O:15])=[O:14])[CH:12]=1>C(Cl)Cl.N1C=CC=CC=1>[N:2]1([S:13]([C:11]2[CH:12]=[C:7]([Br:6])[C:8]([Cl:17])=[N:9][CH:10]=2)(=[O:15])=[O:14])[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 27936265-Bromo-6-chloropyridine-3-sulfonyl chlorideHCID 12308726Azetidine hydrochloride

Product 1

HCID 536296285-(Azetidine-1-sulfonyl)-3-bromo-2-chloropyridineYield 37.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Azetidine hydrochloride (0.32 g, 3.44 mmol) was added to a solution of 3-bromo-2-chloropyridine-5-sulfonyl chloride (1 g, 3.44 mmol) in DCM (4 mL) and pyridine (10 mL) and stirred at RT for 22 hours. The solvent was removed in vacuo and ethyl acetate (30 mL) added. The organic phase was washed with 1M hydrochloric acid (20 mL), water (20 mL), brine (20 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the desired compound (0.4 g).

Workup

  1. customThe solvent was removed in vacuo and ethyl acetate (30 mL)
  2. additionadded
  3. washThe organic phase was washed with 1M hydrochloric acid (20 mL), water (20 mL), brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6360a3694e4a4d0aaa347c9be0fd897e
Source dataset
uspto-grants-2010_01
Patent number
US07642259B2

Reaction notes

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