Sodium Iodide → Benzyl-(2,6-dibromo-3-nitro-pyridin-4-yl)-carbamic acid ethyl ester

HRID 639661Notes

Reaction equation

HRID 639661 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10](=[O:23])[NH:11][C:12]1[CH:17]=[C:16]([Br:18])[N:15]=[C:14]([Br:19])[C:13]=1[N+:20]([O-:22])=[O:21])[CH3:8].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[I-].[Na+]>CC(C)=O>[CH2:7]([O:9][C:10](=[O:23])[N:11]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:12]1[CH:17]=[C:16]([Br:18])[N:15]=[C:14]([Br:19])[C:13]=1[N+:20]([O-:22])=[O:21])[CH3:8]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86614481Ethyl (2,6-dibromo-3-nitropyridin-4-yl)carbamate

Product 1

HCID 86614484Benzyl-(2,6-dibromo-3-nitro-pyridin-4-yl)-carbamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (5.57 g) was added to a stirred solution of (2,6-dibromo-3-nitro-pyridin-4-yl)-carbamic acid ethyl ester (7.44 g) in acetone (100 ml) then benzyl bromide (2.87 ml) was added, followed by sodium iodide (3.63 g). The mixture was left to stir under nitrogen for 36 hours. The reaction mixture was filtered to remove precipitated white solids, concentrated in vacuo, and then partitioned between ethyl acetate (100 ml) and water (100 ml). The organics were dried (MgSO4) and evaporated to a yellow oil. This crude oil was adsorbed onto silica gel and then purified by chromatography on Isco Companion on a silica column (80 g, Redisep) eluting with EtOAc:heptane, increasing the gradient linearly from 10:90 to 50:50. This provided the title compound (7.50 g) as a yellow oil.

Workup

  1. waitThe mixture was left
  2. filtrationThe reaction mixture was filtered
  3. customto remove
  4. customprecipitated white solids
  5. concentrationconcentrated in vacuo
  6. custompartitioned between ethyl acetate (100 ml) and water (100 ml)
  7. dry with materialThe organics were dried (MgSO4)
  8. customevaporated to a yellow oil
  9. custompurified by chromatography on Isco Companion on a silica column (80 g, Redisep)
  10. washeluting with EtOAc
  11. temperatureheptane, increasing the gradient linearly from 10:90 to 50:50

Sources & evidence

ORD record
ord-0edbccfd755b4ca6a28eba14a87d9d17
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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