Sodium Iodide → (2,6-Dibromo-3-nitro-pyridin-4-yl)-(6-methyl-pyridin-3-ylmethyl)-carbamic acid ethyl ester

HRID 639650Notes

Reaction equation

HRID 639650 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].Cl[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([CH3:32])=[N:30][CH:31]=1.[I-].[Na+]>CC(C)=O>[CH2:7]([O:9][C:10](=[O:23])[N: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])[CH2:25][C:26]1[CH:31]=[N:30][C:29]([CH3:32])=[CH:28][CH:27]=1)[CH3:8]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 122143385-(Chloromethyl)-2-methylpyridineHCID 86614481Ethyl (2,6-dibromo-3-nitropyridin-4-yl)carbamate

Product 1

HCID 86614482(2,6-Dibromo-3-nitro-pyridin-4-yl)-(6-methyl-pyridin-3-ylmethyl)-carbamic acid ethyl esterYield 62.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (7.95 g) was added to a stirred solution of (2,6-dibromo-3-nitro-pyridin-4-yl)-carbamic acid ethyl ester (10.62 g) in acetone (100 ml). 5-(chloromethyl)-2-methylpyridine (4.89 g) was then added, followed by sodium iodide (5.18 g). The mixture was left to stir under nitrogen for 18 hours. The reaction mixture was filtered, concentrated in vacuo, and then partitioned between ethyl acetate (100 ml) and water (100 ml). The organics were dried (MgSO4) and evaporated to a dark purple gum, which was columned on Isco Companion on a silica column (330 g, Redisep), eluting with EtOAc:heptane, increasing the gradient linearly from 40:60 to 80:20 over 6 column volumes. This provided the title compound (8.5 g) as a green gum which solidified to a pale green solid on standing.

Workup

  1. waitThe mixture was left
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. custompartitioned between ethyl acetate (100 ml) and water (100 ml)
  5. dry with materialThe organics were dried (MgSO4)
  6. customevaporated to a dark purple gum, which
  7. washeluting with EtOAc
  8. temperatureheptane, increasing the gradient linearly from 40:60 to 80:20 over 6 column volumes

Sources & evidence

ORD record
ord-86159069e7824513889a912227c08e04
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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