Imidazole → 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(dimethyl(2-methyl-2-propyl)silyloxy)propyl)phenyl)-2-propanol

HRID 342012Notes

Reaction equation

HRID 342012 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@@H:20]([OH:33])[CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([OH:32])([CH3:31])[CH3:30])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[C:34]([Si:38](Cl)([CH3:40])[CH3:39])([CH3:37])([CH3:36])[CH3:35].N1C=CN=C1.C1(C)C=CC=CC=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@@H:20]([O:33][Si:38]([CH3:40])([CH3:39])[C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([OH:32])([CH3:31])[CH3:30])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 1140TolueneHCID 28928tert-Butyldimethylsilyl chlorideHCID 54563620C29H28ClNO2

Product 1

HCID 536347942-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(dimethyl(2-methyl-2-propyl)silyloxy)propyl)phenyl)-2-propanol

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To the diol of Step 3 (36.56 g, 79.8 mmol) in 400 mL of CH2Cl2 was added tert-butyl-chloro-dimethylsilane (18.21 g, 121 mmol), imidazole (10.97 g, 161 mmol) and 4-(dimethylamino)pyridine (0.988 g, 8.1 mmol) and the mixture was stirred at r.t. for 3 days. Toluene (400 mL) was then added and the product was filtered through silica with EtOAc:toluene 0:100 to 5:95. The title product was concentrated and stripped with toluene to remove any remaining silyl chloride.

Workup

  1. filtrationthe product was filtered through silica with EtOAc:toluene 0:100 to 5:95
  2. concentrationThe title product was concentrated
  3. customto remove any remaining silyl chloride

Sources & evidence

ORD record
ord-19787b34dc8a4457bb2488d751abbcb0
Source dataset
uspto-grants-1999_01
Patent number
US05856322

Reaction notes

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