Diethyl Ether → HCID 22482395, compound

HRID 2181871Notes

Reaction equation

HRID 2181871 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][CH:7]=[C:8]3[C:13]=2[CH:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1.C[Li].[CH2:17](OCC)C.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][C:25]=1[C:34]([F:37])([F:36])[F:35]>>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([N:6]2[CH:7]([CH3:17])[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)(=[O:32])=[O:31])=[CH:26][C:25]=1[C:34]([F:37])([F:36])[F:35]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 9189PhenanthridineHCID 224823844-Methoxy-3-(trifluoromethyl)benzenesulfonyl chlorideHCID 178418348HCID 178418348, compound

Product 1

HCID 22482395HCID 22482395, compoundYield 44.2%

Procedure

The title compound was prepared from phenanthridine (5.38 g, 30 mmol), 1.4 M methyllithium in diethyl ether (21.8 mL, 30.5 mmol), and 4-methoxy-3-(trifluoromethyl)benzenesulfonyl chloride (8.24 g, 30 mmol) according to the procedure and in the same manner as described in Example 1, step a. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:8) to yield 5-{[4-methoxy-3-(trifluoromethyl)phenyl]sulfonyl}-6-methyl-5,6-dihydrophenanthridine (5.75 g, 13.27 mmol, 44%) as a white solid;

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:8)

Sources & evidence

ORD record
ord-4918139372c842118bdaf3df54ea6932
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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