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

HRID 2181865Notes

Reaction equation

HRID 2181865 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.[F:22][C:23]1[CH:24]=[C:25]([S:31](Cl)(=[O:33])=[O:32])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]>>[F:22][C:23]1[CH:24]=[C:25]([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]=[CH:27][C:28]=1[O:29][CH3:30]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 9189PhenanthridineHCID 27745403-Fluoro-4-methoxybenzene-1-sulfonyl chlorideHCID 178418348HCID 178418348, compound

Product 1

HCID 224822965-[(3-Fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridineYield 44.3%

Procedure

The title compound was prepared from phenanthridine (7.17 g, 40 mmol), 1.4 M methyllithium in diethyl ether (29 mL, 40.6 mmol), and 3-fluoro-4-methoxybenzenesulfonyl chloride (8.99 g, 40 mmol) according to the procedure and in the same manner as described in Example 1, step a. The crude product was purified by re-crystallization from a mixture of ethyl acetate-cyclohexane to yield 5-[(3-fluoro-4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (6.79 g, 17.7 mmol, 44%) as an off-white solid;

Workup

  1. customThe crude product was purified by re-crystallization from a mixture of ethyl acetate-cyclohexane

Sources & evidence

ORD record
ord-da6e86bc60d845689bde7302401fca2a
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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