Diethyl Ether → 5-[(4-Methoxy-3,5-dimethylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

HRID 2181874Notes

Reaction equation

HRID 2181874 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[C:29]([CH3:30])=[CH:28][C:27]([S:31](Cl)(=[O:33])=[O:32])=[CH:26][C:25]=1[CH3:35]>>[CH3:22][O:23][C:24]1[C:29]([CH3:30])=[CH:28][C:27]([S:31]([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:33])=[O:32])=[CH:26][C:25]=1[CH3:35]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 9189PhenanthridineHCID 224823214-Methoxy-3,5-dimethylbenzene-1-sulfonyl chlorideHCID 178418348HCID 178418348, compound

Product 1

HCID 224823695-[(4-Methoxy-3,5-dimethylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridineYield 62%

Procedure

The title compound was prepared from phenanthridine (3.58 g, 20 mmol), 1.4 M methyllithium in diethyl ether (14.5 mL, 20.3 mmol), and 4-methoxy-3,5-dimethylbenzenesulfonyl chloride (4.69 g, 20 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-3,5-dimethylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (4.86 g, 12.4 mmol, 62%) 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-5908052be98044e2a3b585c0069cee09
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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