N-Iodosuccinimide → 2-Butoxy-3-iodo-6-methylpyridin-4-amine

HRID 2192998ノート

反応式

HRID 2192998 の反応式
[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([NH2:12])[CH:9]=[C:8]([CH3:13])[N:7]=1)[CH2:2][CH2:3][CH3:4].[I:14]N1C(=O)CCC1=O>C1COCC1>[CH2:1]([O:5][C:6]1[C:11]([I:14])=[C:10]([NH2:12])[CH:9]=[C:8]([CH3:13])[N:7]=1)[CH2:2][CH2:3][CH3:4]

参加物

4

反応物 2

HCID 120273N-IodosuccinimideHCID 593754742-Butoxy-6-methylpyridin-4-amine

生成物 1

HCID 593754672-Butoxy-3-iodo-6-methylpyridin-4-amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-butoxy-6-methylpyridin-4-amine (31 g, 0.17 mol) was dissolved in THF (500 mL), and then N-iodosuccinimide (32 g, 0.14 mol) was added portionwise at −78° C. The reaction mixture was stirred at the same temperature for 2 min. The reaction was quenched by addition of water, and the resulting mixture was extracted with ethyl acetate (2×600 mL). The combined organic layers were washed with brine (500 mL), dried over sodium sulfate, and concentrated. The crude was purified by silica gel column chromatography (petroleum ether) to afford 2-butoxy-3-iodo-6-methylpyridin-4-amine. 1H NMR (400 MHz, CDCl3): δ 6.10 (s, 1H), 4.49 (m, 2H), 4.29 (t, J=6.4 Hz, 2H), 2.284 (s, 1H), 1.75 (m, 2H), 1.50 (m, 2H), 0.98 (t, J=7.6 Hz, 3H). LRMS calc'd for (C10H151N2O) [M+H]+, 307; found 307.

後処理

  1. customThe reaction was quenched by addition of water
  2. extractionthe resulting mixture was extracted with ethyl acetate (2×600 mL)
  3. washThe combined organic layers were washed with brine (500 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude was purified by silica gel column chromatography (petroleum ether)

出典と根拠

ORDレコード
ord-ebf9111f003b4af5a739664f6af4ba42
出典データセット
uspto-grants-2012_12
特許番号
US08329722B2

反応ノート

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