Dichloromethane → 4-[(6-ethyl-8-fluoro-2-thien-3-ylphenanthridin-5(6H)-yl)sulfonyl]phenol

HRID 2181861Notes

Reaction equation

HRID 2181861 reaction equation
[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[C:10]2[CH:9]=[C:8]([C:18]3[CH:22]=[CH:21][S:20][CH:19]=3)[CH:7]=[CH:6][C:5]=2[N:4]1[S:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32]C)=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH3:2].C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[C:10]2[CH:9]=[C:8]([C:18]3[CH:22]=[CH:21][S:20][CH:19]=3)[CH:7]=[CH:6][C:5]=2[N:4]1[S:23]([C:26]1[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=1)(=[O:25])=[O:24])[CH3:2]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 22482332HCID 22482332, compound

Product 1

HCID 103672334-[(6-ethyl-8-fluoro-2-thien-3-ylphenanthridin-5(6H)-yl)sulfonyl]phenolYield 63%

Procedure

The title compound was prepared from 6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-2-thien-3-yl-5,6-dihydrophenanthridine (0.28 g, 0.58 mmol), cyclohexene (13 mL, 10.5 mmol), and 1 M boron tribromide in dichloromethane (3.5 mL, 3.5 mmol) according to the procedure and in the same manner as described in Example 47, Step b. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:4) to yield 4-[(6-ethyl-8-fluoro-2-thien-3-ylphenanthridin-5(6H)-yl)sulfonyl]phenol as a homogeneous solid (0.17 g, 63%);

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:4)

Sources & evidence

ORD record
ord-e4e965c295c34c54abc331cbb14add7f
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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