Dimethylformamide → 3-Bromo-5-(ethoxymethyl)pyridine

HRID 9382

반응식

HRID 9382 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].I[CH2:21][CH3:22].CN(C=O)C>C1COCC1.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1.[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][O:9][CH2:21][CH3:22])[CH:3]=1

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 2784733(5-Bromo-3-pyridinyl)methanol

생성물 2

HCID 2784733(5-Bromo-3-pyridinyl)methanolHCID 219843463-Bromo-5-(ethoxymethyl)pyridine수율 120.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 57417360Sodium chloride; water용매

실험 절차

(5-Bromopyridin-3-yl)methanol was prepared according to the published procedure (Zhang, N. et al, J. Med. Chem., 45, 2832–2840 (2002)). A solution of (5-bromopyridin-3-yl)methanol (7.39 g, 39.3 mmol) in THF was cooled to 0° C. Sodium bis(trimethylsilyl)amide (39.3 mL of a 1.0 M solution in THF) was added, and the reaction was stirred for 20 minutes. Iodoethane (3.46 mL, 43.2 mmol) and DMF were added, and the reaction was allowed to warm to ambient temperature and stirred overnight. Brine was added, and the aqueous layer was extracted twice with hexanes. The combined organic fractions were concentrated under reduced pressure, and the residue was purified by HPFC (eluting with hexanes:ethyl acetate in a gradient from 100:0 to 70:30) to provide 5.11 g of 3-bromo-5-ethoxymethylpyridine as a colorless oil.

후처리

  1. stirringstirred overnight
  2. extractionthe aqueous layer was extracted twice with hexanes
  3. concentrationThe combined organic fractions were concentrated under reduced pressure
  4. customthe residue was purified by HPFC (
  5. washeluting with hexanes

출처 및 근거

ORD 기록
ord-db1f569af9f74fb396843cd058260599
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091214B2

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