Imidazole → 3-(4-((Tert-butyl(dimethyl)silyl)oxy)phenyl)pyridin-2-amine

HRID 1748007Notes

Reaction equation

HRID 1748007 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:15]([Si:19]([CH3:22])([CH3:21])Cl)([CH3:18])([CH3:17])[CH3:16].N1C=CN=C1.O>CN(C=O)C>[Si:19]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:9][CH:10]=1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 667484774-(2-Aminopyridin-3-yl)phenol

Product 1

HCID 667477073-(4-((Tert-butyl(dimethyl)silyl)oxy)phenyl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(2-aminopyridin-3-yl)phenol (19.8 g), tert-butyldimethylchlorosilane (21.8 mL) and 1H-imidazol (8.69 g) in DMF (200 mL) was stirred at room temperature for 20 hr. To the mixture was added water, and the resulting precipitate was collected by filtration, and then washed with water to give the title compound (30.5 g) as a white solid.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-4c9c5e63f9b94f7783df82c679e75b6e
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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