Imidazole → 3-Bromo-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)pyridine

HRID 21906Notes

Reaction equation

HRID 21906 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1.[C:10]([Si:14](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][Si:14]([C:10]([CH3:13])([CH3:12])[CH3:11])([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 152798563-Bromo-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromopyridin-3-ylmethanol (Chem. Pharm. Bull. 1990, 38, 2446) (29 g, 154 mmoL) and tert-butylchlorodiphenylsilane (47.5 g, 173 mmoL) in CH2Cl2 (500 mL) at r.t., there was added imidazole (15.8 g, 232 mmoL). The mixture was stirred for 1 hr. and filtered. The filtrate was evaporated and the residue chromatographed on silica gel eluting with a 1:7 mixture of EtOAc and hexane, to afford the product as a colorless oil.

Workup

  1. filtrationand filtered
  2. customThe filtrate was evaporated
  3. customthe residue chromatographed on silica gel eluting with a 1:7 mixture of EtOAc and hexane

Sources & evidence

ORD record
ord-35ea8008cfbb4dbebdfdd74306ca8a49
Source dataset
uspto-grants-1995_06
Patent number
US05426109

Reaction notes

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