Dichloromethane → HCID 9999147, compound

HRID 2181822Notes

Reaction equation

HRID 2181822 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C@@H:5]2[CH3:27].C1CCCCC=1.B(Br)(Br)Br.ClCCl>>[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]([S:16]([C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)(=[O:18])=[O:17])[C@@H:5]2[CH3:27]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 69354296HCID 69354296, compound

Product 1

HCID 9999147HCID 9999147, compound

Procedure

The title compound was prepared from (R)-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.74 g, 1.93 mmol), cyclohexene (7.0 mL, 70.0 mmol), and 1 M boron tribromide in dichloromethane (23 mL, 23 mmol) according to the procedure and in the same manner as described in Example 32, Method B, Step b. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:9 to 1:4 gradient), followed by trituration from hot hexane to yield 4-{[(R)-8-fluoro-6-methylphenanthridin-5(6H)-yl]sulfonyl}phenol* as a solid (0.52 g, 73%), m.p. 193° C.

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:9 to 1:4 gradient)

Sources & evidence

ORD record
ord-ec2a881c2c8b44de9189546d5a76c0dc
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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