Imidazole → HCID 58464027, compound

HRID 629211Notes

Reaction equation

HRID 629211 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-6cc09b1dbd974cc1ab6f2352fd879cc7
Source dataset
uspto-grants-2016_04
Patent number
US09315498B2

Reaction notes

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