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

HRID 506955ノート

反応式

HRID 506955 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418647HCID 178418647、化合物触媒2 回HCID 6212Chloroform溶媒

実験手順

(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%)

後処理

  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

出典と根拠

ORDレコード
ord-aa96a7e15a9144afbf143640bbcd5145
出典データセット
uspto-grants-2010_08
特許番号
US07786130B2

反応ノート

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