Ethanesulfonyl chloride → HCID 118500702, compound

HRID 712731Notes

Reaction equation

HRID 712731 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9]N)[CH:5]=[N:6][CH:7]=1.C([N:14](CC)C(C)C)(C)C.[CH2:20]([S:22](Cl)(=[O:24])=[O:23])[CH3:21]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C@H:8]([NH:14][S:22]([CH2:20][CH3:21])(=[O:24])=[O:23])[CH3:9])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11667Ethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 534036822-(5-Bromopyridin-3-yl)ethan-1-amine

Product 1

HCID 118500702HCID 118500702, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a vial is added (1R)-1-(5-bromo(3-pyridyl)ethylamine (300 mg, 1.26 mmol) in 3 ml of CH2Cl2, followed by the addition of N,N-diisopropylethylamine (490 mg, 3.79 mmol). Then ethanesulfonyl chloride (195 mg, 1.52 mmol) is added. The reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with DCM, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude product. Purification by the flash column chromatography affords 278 mg of ethanesulfonic acid [(R)-1-(5-bromo-pyridin-3-yl)-ethyl]-amide.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product
  6. customPurification by the flash column chromatography

Sources & evidence

ORD record
ord-07b33c0091eb4a5e94a728ce8849f3d1
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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