Cyclohexene → HCID 22482381, compound

HRID 2181919Notes

Reaction equation

HRID 2181919 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][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: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][C:7]([F:28])=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8079CyclohexeneHCID 25134Boron tribromideHCID 22482310HCID 22482310, compound

Product 1

HCID 22482381HCID 22482381, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from 2,9-difluoro-5-[(3-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (156 mg, 0.39 mmol), cyclohexene (760 μL, 7.7 mmol), and 1.0 M solution of boron tribromide in dichloromethane (2.33 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%-50% methyl tert-butyl ether in hexane, to afford the desired product (139 mg, 92%) as a white solid, m.p. 165.5-171° 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%-50% methyl tert-butyl ether in hexane

Sources & evidence

ORD record
ord-214c1ff2aa254acb8151d1406a43a4d0
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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