Cyclohexene → 3-[(2-Fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol

HRID 2181906Notes

Reaction equation

HRID 2181906 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:13]2[N:12]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25]C)[CH:20]=3)(=[O:18])=[O:17])[CH:11]([CH3:27])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1.C1CCCCC=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:15]=[CH:14][C:13]2[N:12]([S:16]([C:19]3[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=3)(=[O:18])=[O:17])[CH:11]([CH3:27])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8079CyclohexeneHCID 25134Boron tribromideHCID 224823522-Fluoro-5-[(3-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Product 1

HCID 224822783-[(2-Fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenolYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from 2-fluoro-5-[(3-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (100 mg, 0.26 mmol), cyclohexene (528 μL, 5.2 mmol), and 1.0 M solution of boron tribromide in dichloromethane (1.6 mL) according to the procedure and in the same manner as described in Example 105, step e. The volatile components were removed in vacuo, and the crude residue was purified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g), eluting with a gradient of 5%-30% methyl tert-butyl ether in hexane, to afford the desired compound (86 mg, 89%) as a solid, m.p. 195-196° C.;

Workup

  1. customThe volatile components were removed in vacuo
  2. customthe crude residue was purified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g)
  3. washeluting with a gradient of 5%-30% methyl tert-butyl ether in hexane

Sources & evidence

ORD record
ord-418dd0e0b15246a686c76ca756eff0b7
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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