Dichloromethane → 3-Bromo-5-(((tert-butyldimethylsilyl)oxy)methyl)pyridine

HRID 1721791

反応式

HRID 1721791 の反応式
C(Cl)Cl.Cl.[Br:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([CH2:12][OH:13])[CH:11]=1.C(N(CC)CC)C.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C(OCC)C>[Br:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([CH2:12][O:13][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH:11]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 23445112(5-Bromopyridin-3-yl)methanol hydrochloride

生成物 1

HCID 219840913-Bromo-5-(((tert-butyldimethylsilyl)oxy)methyl)pyridine収率 81.2%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a methylene chloride solution (20 mL) of 3-bromo-5-(hydroxymethyl)pyridine hydrochloride (described in example 69a) (1.00 g, 4.48 mmol) under nitrogen was added triethylamine (2.50 mL, 17.9 mmol, 4 eq) and tert-butyldimethylsilyl chloride (0.75 g, 5.0 mmol, 1.1 eq). The resulting solution was heated to reflux for 18 h, cooled to room temperature and diluted with diethyl ether (200 mL). The organic phase was washed with 2.5N NaOH (1×100 mL), water (3×100 mL) and saturated brine (1×100 mL). The ether solution was dried over anhydrous magnesium sulfate, filtered, and reduced to an colorless oil. The procedure resulted in 1.10 g (81%) of the title compound. The product required no additional purification. TLC analysis (Rf 0.19, ethyl acetate) MS (CI, CH4) m/z 302 (M+1,100), 304 (96), 330 (M+29,4), 332 (4).

後処理

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 18 h
  3. washThe organic phase was washed with 2.5N NaOH (1×100 mL), water (3×100 mL) and saturated brine (1×100 mL)
  4. dry with materialThe ether solution was dried over anhydrous magnesium sulfate
  5. filtrationfiltered

出典と根拠

ORDレコード
ord-fa2f677dda304512bc3d747154cab06e
出典データセット
uspto-grants-1996_04
特許番号
US05512575

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