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

HRID 1490215

반응식

HRID 1490215 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-15b1e80b41d048c58a1692b4aa85ca54
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05681840

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