Imidazole → Pyridine, 2-bromo-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

HRID 2239359Notes

Reaction equation

HRID 2239359 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1.[C:10]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH2:8][O:9][Si:14]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:16])[CH3:15])[N:7]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 3517811(6-Bromopyridin-2-yl)methanol

Product 1

HCID 11483477Pyridine, 2-bromo-6-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(6-Bromopyridin-2-yl)methanol (5.0 g, 26.6 mmol), DMAP (0.65 g, 5.3 mmol), tert-butyl(chloro)dimethylsilane (4.8 g, 31.9 mmol) and imidazole (2.3 g, 34.0 mmol) was mixed in DCM (100 mL) and stirred at room temperature over night. The reaction mixture was washed with water (3×100 mL), dried over a phase separator and concentrated in vacuo to give the product as an oil. Yield: 8.3 g (103%) 1H NMR (400 MHz, CDCl3) δ 7.55 (t, 1H, J=7.87 Hz), 7.46 (d, 1H, J=7.87 Hz), 7.32 (d, 1H, J=7.87 Hz), 0.94 (s, 9H), 0.10 (s, 6H).

Workup

  1. washThe reaction mixture was washed with water (3×100 mL)
  2. customdried over a phase separator
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f0e9637f98948f0a77a50e81f2750ee
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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