Imidazole → HCID 66934192, compound

HRID 391077Notes

Reaction equation

HRID 391077 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.N1C=CN=C1.[Si:15](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 5200169(5-Bromopyridin-2-yl)methanol

Product 1

HCID 66934192HCID 66934192, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-bromo-pyridin-2-yl)-methanol (300 mg) in dichloromethane (20 mL) was added imidazole (217 mg) and tert-butyldiphenylsilyl chloride (0.41 mL) and the reaction stirred at room temperature for 16 h. the reaction was quenched with water (20 mL) and extracted into dichloromethane (2×30 mL). The organic layers were dried (MgSO4) and reduced in vacuo to give 5-bromo-2-(tert-butyl-diphenylsilanyloxymethyl)-pyridine as an oil.

Workup

  1. customwas quenched with water (20 mL)
  2. extractionextracted into dichloromethane (2×30 mL)
  3. dry with materialThe organic layers were dried (MgSO4)

Sources & evidence

ORD record
ord-5fe817d5c4f54c31aa58e64a30a250d5
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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