Cyclohexene → HCID 22482258, compound

HRID 2181917Notes

Reaction equation

HRID 2181917 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][C:7]([F:28])=[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:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:11]([CH3:27])[C:10]3[C:5](=[CH:6][C:7]([F:28])=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8079CyclohexeneHCID 25134Boron tribromideHCID 22482292HCID 22482292, compound

Product 1

HCID 22482258HCID 22482258, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from 2,9-difluoro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (150 mg, 0.37 mmol), cyclohexene (757 μL, 7.5 mmol), and 1.0 M solution of boron tribromide in dichloromethane (2.24 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 on a Biotage® 40 Mi column of prepacked silica gel (90 g), eluting with a gradient of 5%-50% methyl tert-butyl ether in hexane, to afford the desired compound (117 mg, 81%) as a white solid, m.p. 194-196° C.;

Workup

  1. customThe volatile components were removed in vacuo
  2. customthe crude residue was purified on a Biotage® 40 Mi column of prepacked silica gel (90 g)
  3. washeluting with a gradient of 5%-50% methyl tert-butyl ether in hexane

Sources & evidence

ORD record
ord-d85d7f92af704477be5bad8cd5d28a0c
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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