Imidazole → HCID 131722145, compound

HRID 1856707Notes

Reaction equation

HRID 1856707 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH:9]1C=CN=[CH:10]1.[Br:14][C:15]1[CH:32]=[CH:31][C:18]([S:19][CH2:20][C@H:21]([OH:30])[CH2:22][CH2:23][C:24]2C=NC=[CH:28][CH:29]=2)=[CH:17][CH:16]=1.Cl[CH2:34]Cl>>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([S:19][C@@H:20]([CH:21]([O:30][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:22][C:23]2[CH:10]=[N:9][CH:28]=[CH:29][CH:24]=2)[CH3:34])=[CH:31][CH:32]=1

Participants

5

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 131722146HCID 131722146, compound

Product 1

HCID 131722145HCID 131722145, compound

Procedure

tert-Butyldimethylsilyl chloride (0.452 g), followed by imidazole (0.408 g) were added to a solution of (2R)-1-(4-bromothiophenoxy)-4-(pyridin-3-yl)-2-butanol (Example 41a), 0.67 g) in anhydrous dichloromethane (20 ml), under an inert atmosphere. The mixture was stirred overnight at room temperature. The precipitate was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with hexane:ethyl acetate (1:9 to 1:1) to give the sub-title compound as an oil (0.76 g).

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography over silica eluting with hexane:ethyl acetate (1:9 to 1:1)

Sources & evidence

ORD record
ord-4254260744a84714bf3913bdfcd0a82b
Source dataset
uspto-grants-2000_11
Patent number
US06143751

Reaction notes

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