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

HRID 9382

反応式

HRID 9382 の反応式
[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

参加物

8

反応物 4

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

生成物 2

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-db1f569af9f74fb396843cd058260599
出典データセット
uspto-grants-2006_08
特許番号
US07091214B2

関連ノート

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