4-Methoxybenzyl alcohol → 3-Benzyloxy-6-iodo-2-(4-methoxybenzyloxy)pyridine

HRID 625967

반응식

HRID 625967 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][OH:10])=[CH:7][CH:8]=1.[H-].[Na+].[H][H].[CH2:15]([O:22][C:23]1[C:24](Br)=[N:25][C:26]([I:29])=[CH:27][CH:28]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C.O>[CH2:15]([O:22][C:23]1[C:24]([O:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:25][C:26]([I:29])=[CH:27][CH:28]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

7

반응물 4

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 110255633-(Benzyloxy)-2-bromo-6-iodopyridineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 866754893-Benzyloxy-6-iodo-2-(4-methoxybenzyloxy)pyridine수율 81.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a 0° C. solution of p-methoxybenzyl alcohol (13.83 g, 100 mmol) in 33 mL DMF was added sodium hydride (4 g, 100 mmol) slowly. The mixture was stirred at room temperature until evolution of hydrogen had ceased, and crude 3-(benzyloxy)-2-bromo-6-iodopyridine (13.01 g, 33.4 mmol) was added. The resulting solution was heated to 100° C. for 1 h under nitrogen. After cooling, the mixture was diluted with water and extracted with ethyl acetate. The aqueous layer was removed and discarded. The organic layer was collected, dried over anhydrous magnesium sulfate and purified by silica gel chromatography to afford 3-(benzyloxy)-6-iodo-2-[(4-methoxybenzyl)oxy]pyridine (12.1 g, 27.1 mmol, 81% yield). ES-MS (M+H)+=448.

후처리

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. customThe aqueous layer was removed
  4. customThe organic layer was collected
  5. dry with materialdried over anhydrous magnesium sulfate
  6. custompurified by silica gel chromatography

출처 및 근거

ORD 기록
ord-f9eb8841c74a40c78695c720eed21e84
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309199B2

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