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

HRID 43259노트

반응식

HRID 43259 반응식
[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]

참가 물질

5

반응물 3

HCID 807IodineHCID 5323848N-(6-methoxypyridin-3-yl)pivalamide2회HCID 178418306HCID 178418306, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-fa494021de364114be4544eef00f9fc6
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536339B2

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