Imidazole → HCID 67252345, compound

HRID 2042038Notes

Reaction equation

HRID 2042038 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][CH2:15][OH:16])[CH:8]=2)=[CH:4][C:3]=1[F:19].N1C=CN=C1.[CH3:25][C:26]([Si:29](Cl)([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CN(C=O)C>[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][CH2:15][O:16][Si:29]([C:26]([CH3:28])([CH3:27])[CH3:25])([CH3:31])[CH3:30])[CH:8]=2)=[CH:4][C:3]=1[F:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67254928HCID 67254928, compound

Product 1

HCID 67252345HCID 67252345, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example A8 (0.263 g, 1.0 mmol), imidazole (0.0749 g, 1.1 mmol) and TBSCl (0.181 g, 1.2 mmol) in DMF (10 mL) was stirred at RT overnight. Solvent was removed under reduced pressure. The residue was quenched with H2O (10 mL) and the pH was adjusted to ˜8 by using NaHCO3. The aqueous solution was extracted with EtOAc (3×20 mL) and the combined organic layers were dried (MgSO4), concentrated in vacuo and purified by chromatography to afford 4-(4-amino-3-fluorophenoxy)-N-(2-(tert-butyldimethylsilyloxy)ethyl)pyridin-2-amine (0.252 g, 67% yield) as a light yellow oil. MS (ESI) m/z: 378.3 (M+H+).

Workup

  1. customSolvent was removed under reduced pressure
  2. customThe residue was quenched with H2O (10 mL)
  3. extractionThe aqueous solution was extracted with EtOAc (3×20 mL)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-c566df1c1141433bb73ed14eab86f42f
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

Loading…