Ethyl chloroformate → (2-Bromo-pyridin-3-yl)carbamic acid ethyl ester

HRID 2080013Notes

Reaction equation

HRID 2080013 reaction equation
[NH2:1][C:2]1[C:3]([Br:8])=[N:4][CH:5]=[CH:6][CH:7]=1.Cl[C:10]([O:12][CH2:13][CH3:14])=[O:11]>N1C=CC=CC=1.[Cl-].[Na+].O>[CH2:13]([O:12][C:10](=[O:11])[NH:1][C:2]1[C:3]([Br:8])=[N:4][CH:5]=[CH:6][CH:7]=1)[CH3:14]

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 6428163-Amino-2-bromopyridine

Product 1

HCID 13803673(2-Bromo-pyridin-3-yl)carbamic acid ethyl esterYield 28%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3-Amino-2-bromopyridine described in Preparation Example S-1 (1.4 g, 8.1 mmol) was dissolved in pyridine (10 mL), ethyl chloroformate (0.93 mL, 9.7 mmol) was added dropwise on an ice bath, and the solution was stirred for 2 hours at room temperature. After the reaction was completed, the reaction solution was poured into brine, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then evaporated, the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4), and the title compound (0.56 g, 2.3 mmol, 28%) was obtained.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customevaporated
  4. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-5eedabd02d4c4f6faaf2d614f91ac49a
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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