Cyclohexene → HCID 22482302, compound

HRID 2181897Notes

Reaction equation

HRID 2181897 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([CH:12]([CH3:27])[N:13]([S:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([O:25]C)[CH:20]=4)(=[O:18])=[O:17])[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3.C1CCCCC=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([CH:12]([CH3:27])[N:13]([S:16]([C:19]4[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=4)(=[O:18])=[O:17])[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

5

Reactant 3

HCID 8079CyclohexeneHCID 25134Boron tribromideHCID 224822573-Fluoro-5-[(3-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

Product 1

HCID 22482302HCID 22482302, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from 3-fluoro-5-[(3-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (350 mg, 0.91 mmol), cyclohexene (1.85 mL, 18 mmol), and 1.0 M solution of boron tribromide in dichloromethane (5.5 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 30%-50% methyl tert-butyl ether in hexane, to afford the desired compound (77 mg, 30%) as a solid, m.p. 164-167° 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 30%-50% methyl tert-butyl ether in hexane

Sources & evidence

ORD record
ord-829b066545884b5f81e34e2b25aacc63
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

Loading…