Imidazole → 5-((Tert-butyl(diphenyl)silyl)oxy)-2-chloro-3-fluoropyridine

HRID 2277299Notes

Reaction equation

HRID 2277299 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[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.CN(C=O)C>O>[Si:14]([O:8][C:5]1[CH:4]=[C:3]([F:9])[C:2]([Cl:1])=[N:7][CH:6]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 404247372-Chloro-3-fluoro-5-hydroxypyridine

Product 1

HCID 867313815-((Tert-butyl(diphenyl)silyl)oxy)-2-chloro-3-fluoropyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-chloro-5-fluoropyridin-3-ol (13.1 g), tert-butyl (chloro)diphenylsilane (27.7 mL), 1H-imidazole (7.25 g) and DMF (100 mL) was stirred at room temperature overnight. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (29.5 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layer were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-82c23df98cdb44979f385cc131593199
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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