Imidazole → HCID 42626277, compound

HRID 2236547Notes

Reaction equation

HRID 2236547 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH3:13].[CH:14]([Si:17](Cl)([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])([CH3:16])[CH3:15].N1C=CN=C1>ClCCl>[Cl:1][C:2]1[C:3]([O:10][CH2:11][CH2:12][CH3:13])=[CH:4][CH:5]=[C:6]([CH2:8][O:9][Si:17]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:14]([CH3:16])[CH3:15])[N:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 42626276HCID 42626276, compound

Product 1

HCID 42626277HCID 42626277, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (6-chloro-5-propoxy-pyridin-2-yl)-methanol (0.93 g, 4.61 mmole), 20 mL of dichloromethane, tri(isopropyl)silyl chloride (1.0 g, 5.19 mmole) and imidazole (0.47 g, 6.9 mmole) is stirred overnight at ambient temperature. The reaction mixture is washed with water, dried over sodium sulfate, filtered and evaporated in-vacuo to give an oil which is chromatographed on silica gel with 10:1 hexane/ethyl acetate to give 2-chloro-3-propoxy-6-triisopropylsilanyloxymethyl-pyridine as a clear liquid, 1.06 g, (64%); MS (ES+): m/z 358.2, 360.2 (M+H). A portion of this (716 mg, 2.0 mmole) and 5 mL of 1M sodium benzyloxide in benzyl alcohol is heated in a microwave reactor 5 minutes at 120° C. The reaction mixture is cooled, transferred to a separatory funnel with ethyl acetate, washed with water, the organic layer is dried, filtered, evaporated and chromatographed on silica gel with hexane/ethyl acetate to give a clear liquid, 524 mg, (61%); MS (ES+): m/z 430.3 (M+H).

Workup

  1. washThe reaction mixture is washed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated in-vacuo
  5. customto give an oil which
  6. customis chromatographed on silica gel with 10:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-d14d0876de1c4a6b80cd55de2947f656
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…