Acetic Acid → HCID 66788233, compound

HRID 1623510Notes

Reaction equation

HRID 1623510 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH2:9])[CH:5]=[N:6][CH:7]=1.[H-].[Na+].[CH:12]([S:15](Cl)(=[O:17])=[O:16])([CH3:14])[CH3:13].C(O)(=O)C>CN(C=O)C.[Cl-].[Na+].O.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][S:15]([CH:12]([CH3:14])[CH3:13])(=[O:17])=[O:16])[CH:5]=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 824082-Propanesulfonyl chlorideHCID 229922643-(Aminomethyl)-5-bromopyridine

Product 1

HCID 66788233HCID 66788233, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 5-bromo-3-pyridinemethanamine (CAS#135124-70-8, 200 mg, 0.77 mmol) in DMF (8 mL) at 0° C. was added sodium hydride (60% oil dispersion, 150 mg, 3.8 mmol) followed by isopropylsulfonyl chloride (0.13 mL, 1.16 mmol). The reaction was stirred for 30 minutes and then diluted with brine and dichloromethane. The pH of the aqueous layer was adjusted to ca. 7 by the addition of acetic acid and the layers were separated. The aqueous layer was extracted two additional times with dichloromethane, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated to provide propane-2-sulfonic acid (5-bromo-pyridin-3-ylmethyl)-amide without the need for further purification; MS: (ES+) m/z 292.9 (M+H)+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted two additional times with dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-be327f72b230494f97c6ff1a1d7777a3
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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