Sodium Carbonate → HCID 117672591, compound

HRID 712642Notes

Reaction equation

HRID 712642 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][NH2:9].C([O-])([O-])=O.[Na+].[Na+].[CH2:16]([S:18](Cl)(=[O:20])=[O:19])[CH3:17]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][S:18]([CH2:16][CH3:17])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11667Ethanesulfonyl chlorideHCID 469079661-(3-Bromopyridin-4-yl)methanamine

Product 1

HCID 117672591HCID 117672591, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3-bromopyridin-4-yl) methanamine (720 mg, 3.9 mmol) in DCM (20 mL) is added Na2CO3 (1.2 g, 11 mmol). Then ethanesulfonyl chloride (740 mg, 5.8 mmol) is added dropwise under N2 atmosphere at 0° C. The mixture is stirred at room temperature for 16 hrs and it is diluted with DCM. The mixture is washed with water and brine, dried over Na2SO4, filtered and concentrated. The crude product is purified by flash column chromatography to give 600 mg of ethanesulfonic acid (3-bromo-pyridin-4-ylmethyl)-amide.

Workup

  1. washThe mixture is washed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by flash column chromatography

Sources & evidence

ORD record
ord-0de81677fc25489cb9459418f110ac18
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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