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

HRID 1053783

反応式

HRID 1053783 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b9e6ce65af5442439becdfbe4747c222
出典データセット
uspto-grants-2016_07
特許番号
US09394264B2

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