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

HRID 1175860Notes

Reaction equation

HRID 1175860 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-25c7c075aa284cb699dc5bb9204fde04
Source dataset
uspto-grants-2010_11
Patent number
US07842694B2

Reaction notes

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