Methyl iodide → Benzyl (5-iodo-2-methoxypyridin-3-yl)carbamate

HRID 506955Notes

Reaction equation

HRID 506955 reaction equation
[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]1[C:12](=[O:18])[NH:13][CH:14]=[C:15]([I:17])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20]I>C(=O)([O-])[O-].[Ag+2].C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]1[C:12]([O:18][CH3:20])=[N:13][CH:14]=[C:15]([I:17])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 10044624Benzyl 5-iodo-2-oxo-1,2-dihydropyridin-3-ylcarbamate

Product 1

HCID 59432848Benzyl (5-iodo-2-methoxypyridin-3-yl)carbamateYield 102.8%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalyst2×HCID 6212ChloroformSolvent

Procedure

(5-Iodo-2-oxo-1,2-dihydro-pyridin-3-yl)-carbamic acid benzyl ester 3 (551 g, 1.49 mol, 1.0 Eq.) was charged to a flask followed by CHCl3 (7.4 L). In the dark, silver carbonate (528.9 g, 1.92 mol, 1.3 Eq.) and methyl iodide (940 mL, 15.1 mol, 10.1 Eq.) were charged to the flask and the reaction allowed to stir at ambient temperature overnight. LC analysis showed approximately 68% conversion to product, so a further mount of silver carbonate (35 g, 127 mmol, 0.09 Eq.) was added and the reaction allowed to stir at ambient temperature for 66 hours. The reaction mixture was filtered through celite (300 g) and the filter pad washed with CHCl3 (5×500 mL). The combined organic extracts were concentrated in vacuo to give an orange oil (588.5 g) which was split into two batches and purified by column chromatography using silica gel (2×2 Kg) eluting with 1;1 EtOAc/hexane to give the desired product as an orange oil which solidified to a pale pink solid on standing (495.7 g, 1.29 mol, 87%)

Workup

  1. stirringto stir at ambient temperature for 66 hours
  2. filtrationThe reaction mixture was filtered through celite (300 g)
  3. washthe filter pad washed with CHCl3 (5×500 mL)
  4. concentrationThe combined organic extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-aa96a7e15a9144afbf143640bbcd5145
Source dataset
uspto-grants-2010_08
Patent number
US07786130B2

Reaction notes

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