Imidazole → HCID 58464027, compound

HRID 1917537Notes

Reaction equation

HRID 1917537 reaction equation
[OH:1][CH:2]1[C:6](=[O:7])[N:5]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][N:9]=2)[C:4](=[O:15])[C:3]1([CH3:17])[CH3:16].N1C=CN=C1.[C:23]([Si:27]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)Cl)([CH3:26])([CH3:25])[CH3:24].C([O-])(O)=O.[Na+]>ClCCl>[C:23]([Si:27]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[O:1][CH:2]1[C:6](=[O:7])[N:5]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][N:9]=2)[C:4](=[O:15])[C:3]1([CH3:17])[CH3:16])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 516892Sodium BicarbonateHCID 58464066HCID 58464066, compound

Product 1

HCID 58464027HCID 58464027, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2.4 g, 3.47 mmol, 50%) (4RS)-4-Hydroxy-1-(5-iodo-pyridin-2-yl)-3,3-dimethyl-pyrrolidine-2,5-dione (Example 14, step 2) was dissolved in dichloromethane (20 ml). Imidazole (520 mg, 7.63 mmol) and tert-butyldiphenylchlorosilane (1.0 g, 3.64 mmol) were added at room temperature and the mixture was stirred for 3 hours at room temperature. Sat. NaHCO3 solution was added and the mixture was extracted with dichloromethane. The organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (ethyl acetate/heptane gradient 0:100 to 30:70). The desired compound was obtained as a white solid (1.5 g, 74% yield), MS: m/e=585.1 (M+H+).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by flash chromatography on silica gel (ethyl acetate/heptane gradient 0:100 to 30:70)

Sources & evidence

ORD record
ord-c69ad958caca42e99d8c1f9efd70f5af
Source dataset
uspto-grants-2013_12
Patent number
US08618296B2

Reaction notes

Loading…