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

HRID 2283473ノート

反応式

HRID 2283473 の反応式
[OH:1][C:2]1[C:7]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]([I:19])=[CH:4][N:3]=1.[CH3:20]I>C(Cl)(Cl)Cl>[I:19][C:5]1[CH:6]=[C:7]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2]([O:1][CH3:20])=[N:3][CH:4]=1

参加物

4

反応物 2

HCID 6328Methyl iodideHCID 178522276HCID 178522276、化合物

生成物 1

HCID 59432848Benzyl (5-iodo-2-methoxypyridin-3-yl)carbamate収率 53.6%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a solution of benzyl (2-hydroxy-5-iodopyridin-3-yl)carbamate (16 g, 43 mmol) in CHCl3 (250 mL) was added Ag2CO3 (16.1 g, 58.4 g) and methyl iodide (27.0 mL, 434 mmol) in the dark, and the mixture stirred at RT for overnight. The solid was removed by filtration and the solvent was concentrated and purified by combi-flash (ISCO, 40g silica, UV254, 5:1 pet ether/ethyl acetate) to afford benzyl (5-iodo-2-methoxypyridin-3-yl)carbamate (8.85 g, 53% yield) as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.61 (br, 1H), 7.98 (d, J=1.6 Hz, 1H), 7.35-7.42 (m, 5H), 7.12 (s, 1H), 5.21 (s, 2H), 3.95 (s, 3H); MS (ES) m/z 385 (M+H).

後処理

  1. customThe solid was removed by filtration
  2. concentrationthe solvent was concentrated
  3. custompurified by combi-flash (ISCO, 40g silica, UV254, 5:1 pet ether/ethyl acetate)

出典と根拠

ORDレコード
ord-954555dc8a2c48878e91d4c82f3d31e9
出典データセット
uspto-grants-2015_09
特許番号
US09145393B2

反応ノート

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