tert-Butyldimethylsilyl chloride → 4-Bromo-2-(((tert-butyldimethylsilyl)oxy)methyl)pyridine

HRID 1053783

반응식

HRID 1053783 반응식
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:9])[CH:3]=1.[C:10]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][O:9][Si:14]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:16])[CH3:15])[CH:3]=1

참가 물질

4

반응물 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 14761462(4-Bromopyridin-2-yl)methanol

생성물 1

HCID 583550294-Bromo-2-(((tert-butyldimethylsilyl)oxy)methyl)pyridine수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirring solution of (4-bromopyridin-2-yl)methanol (1.50 g, 8.0 mmol) in DCM (4 mL) was added tert-butylchlorodimethylsilane (1.20 g, 8.0 mmol) following by TEA (1.60 g, 12.0 mmol). The reaction mixture was stirred at room temperature for 12 h then washed with brine and EA. The combined organic layers were dried over MgSO4, filtered, and concentrated to yield an amber liquid. The crude product was purified by chromatography (EA/Hexanes) to produce 1.67 g (70%) of 4-bromo-2-((tert-butyldimethylsilyloxy)methyl)pyridine INT-70 as a light yellow liquid. LCMS-ESI (m/z) calculated for C12H20BrNOSi: 302.3; found 303.0 [M+H]+, tR=4.87 min (Method 1). 1H NMR (400 MHz, CDCl3) δ 8.30 (d, J=5.3, 1H), 7.68 (dd, J=1.9, 0.7, 1H), 7.35-7.24 (m, 1H), 4.80 (s, 2H), 0.99-0.86 (m, 9H), 0.16-0.06 (m, 6H).

후처리

  1. washthen washed with brine and EA
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield an amber liquid
  6. customThe crude product was purified by chromatography (EA/Hexanes)

출처 및 근거

ORD 기록
ord-b9e6ce65af5442439becdfbe4747c222
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394264B2

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