Cyclohexene → 4-[(2-Fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol

HRID 2181903Notes

Reaction equation

HRID 2181903 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][C:22]([O:25]C)=[CH:21][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]=[CH:21][C:22]([OH:25])=[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 224823152-Fluoro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Product 1

HCID 224823504-[(2-Fluoro-6-methylphenanthridin-5(6H)-yl)sulfonyl]phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from 2-fluoro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (220 mg, 0.57 mmol), cyclohexene (1.2 mL, 11.5 mmol), and 1.0 M solution of boron tribromide in dichloromethane (3.4 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 product (164 mg, 77%) as a solid, m.p. 216-218° 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-2a9eaa8b7d1d444296bd87b60bea269f
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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