Iodine → N-(4-Iodo-6-methoxy-3-pyridinyl)-2,2-dimethylpropanamide

HRID 2384489ノート

反応式

HRID 2384489 の反応式
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:5][CH:4]=1.[Li]C(C)(C)C.[I:21]I>C1COCC1>[I:21][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[N:8]=[CH:7][C:6]=1[NH:9][C:10](=[O:15])[C:11]([CH3:12])([CH3:14])[CH3:13]

参加物

5

反応物 3

HCID 807IodineHCID 5323848N-(6-methoxypyridin-3-yl)pivalamide2 回HCID 178418306HCID 178418306、化合物

生成物 1

HCID 21581652N-(4-Iodo-6-methoxy-3-pyridinyl)-2,2-dimethylpropanamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of N-(6-methoxypyridin-3-yl)pivalamide (Compound 1, 7.4 g, 35.6 mmol) in anhydrous THF (200 ml) at −78° C. under argon was added t-BuLi (1.7 M in pentane, 52 ml, 89.0 mmol) slowly. After stirred at −78° C. for 1 h, a solution of I2 (22.6 g, 89.0 mmol) in anhydrous THF (100 ml) at −78° C. was cannulated into the reaction over 20 min and the reaction was stirred for 15 min at −78° C. The cooling bath was then removed and the reaction stirred for 30 min, quenched cautiously with ice, extracted with CH2Cl2. The organic layer was dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes) to yield the title compound.

後処理

  1. stirringthe reaction was stirred for 15 min at −78° C
  2. customThe cooling bath was then removed
  3. stirringthe reaction stirred for 30 min
  4. customquenched cautiously with ice
  5. extractionextracted with CH2Cl2
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes)

出典と根拠

ORDレコード
ord-e5de1b0cf06c47f283b798a40369c6d7
出典データセット
uspto-grants-2012_09
特許番号
US08263767B2

反応ノート

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