Imidazole → HCID 86730058, compound

HRID 1504601Notes

Reaction equation

HRID 1504601 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.[CH3:10][C:11]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1>C1COCC1>[Si:14]([O:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[N:7][CH:6]=1)([C:11]([CH3:13])([CH3:12])[CH3:10])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 177161(6-Chloropyridin-3-yl)methanol

Product 1

HCID 86730058HCID 86730058, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (6-chloropyridin-3-yl)methanol (800 mg, 5.6 mmol) and TBSCl (1000 mg, 6.7 mmol) in THF (15 mL) was added imidazole (455 mg, 6.7 mmol) and the reaction mixture was stirred at rt for 24 h. The mixture was concentrated under vacuum to about ¼ of the original volume and then diluted with EtOAc (30 mL). The resulting mixture was washed with water, aqueous 5% KH2PO4 (30 mL), saturated NaHCO3 (20 mL) and brine (20 mL) sequentially. The organic phase was dried, filtered and concentrated to give the desired product as colorless oil (800 mg, 54%). [LCMS: RtA=1.89 min, m/z 258.2 [M+H]+].

Workup

  1. concentrationThe mixture was concentrated under vacuum to about ¼ of the original volume
  2. additiondiluted with EtOAc (30 mL)
  3. washThe resulting mixture was washed with water, aqueous 5% KH2PO4 (30 mL), saturated NaHCO3 (20 mL) and brine (20 mL) sequentially
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5ed977188813461c898d09063761e709
Source dataset
uspto-grants-2015_12
Patent number
US09216182B2

Reaction notes

Loading…