4-Methoxybenzyl alcohol → 3-Bromo-2-fluoro-5-((4-methoxybenzyloxy)methyl)pyridine

HRID 1621439

반응식

HRID 1621439 반응식
[Br:1][C:2]1[C:3]([F:10])=[N:4][CH:5]=[C:6]([CH2:8]Br)[CH:7]=1.[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=1.[Al]>CC#N.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.[Ag-]=O>[Br:1][C:2]1[C:3]([F:10])=[N:4][CH:5]=[C:6]([CH2:8][O:18][CH2:17][C:16]2[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[CH:7]=1

참가 물질

7

반응물 3

HCID 77384-Methoxybenzyl alcoholHCID 5359268AluminumHCID 595482443-Bromo-5-(bromomethyl)-2-fluoropyridine

생성물 1

HCID 595482913-Bromo-2-fluoro-5-((4-methoxybenzyloxy)methyl)pyridine수율 24%

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 178418778HCID 178418778, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

3-Bromo-5-(bromomethyl)-2-fluoropyridine (5.63 g, 20.9 mmol) was dissolved in MeCN (135 mL) and 4-methoxybenzyl alcohol (5.20 mL, 41.9 mmol), silver (I) oxide (7.169 g, 30.9 mmol), and tetrabutylammonium iodide (2.208 g, 5.98 mmol) were added. The reaction flask was covered with aluminum foil and the reaction was stirred under nitrogen at room temperature overnight. The reaction was filtered through a pad of Celite® (diatomaceous earth), washing with DCM, MeOH and MeCN. The filtrate was concentrated and purified on a silica gel column (3:1 to 2:1 to 3:2 hexanes/DCM to 3:2 DCM/hexanes to 2:1 DCM/hexanes to 3:1 DCM/hexanes to DCM) to give 3-Bromo-2-fluoro-5-((4-methoxybenzyloxy)methyl)pyridine (1.62 g, 24%). MS (ESI pos. ion) m/z 326/328 (M+H)+.

후처리

  1. filtrationThe reaction was filtered through a pad of Celite® (diatomaceous earth)
  2. washwashing with DCM, MeOH and MeCN
  3. concentrationThe filtrate was concentrated
  4. custompurified on a silica gel column (3:1 to 2:1 to 3:2 hexanes/DCM to 3:2 DCM/hexanes to 2:1 DCM/hexanes to 3:1 DCM/hexanes to DCM)

출처 및 근거

ORD 기록
ord-ab5a002a5d574e6f8c2231af6515db9c
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772480B2

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