Dichloromethane → HCID 22482370, compound

HRID 2181935Notes

Reaction equation

HRID 2181935 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:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:7]=[CH:6][C:5]=2[N:4]1[S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33]C)=[CH:29][CH:28]=1)(=[O:26])=[O:25])[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:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:7]=[CH:6][C:5]=2[N:4]1[S:24]([C:27]1[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=1)(=[O:26])=[O:25])[CH3:2]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 22482388HCID 22482388, compound

Product 1

HCID 22482370HCID 22482370, compound

Procedure

A stirred suspension of 6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-2-pyridin-3-yl-5,6-dihydrophenanthridine (0.24 g, 0.51 mmol) and cyclohexene (11.4 mL), 9.22 mmol) was treated at room temperature under nitrogen with a solution of 1.0 boron tribromide in dichloromethane (3.1 mL, 3.1 mmol). After stirring for 20 hours at room temperature, the reaction was quenched with a saturated, aqueous sodium bicarbonate solution (100 mL), and extracted with dichloromethane (6×20 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent concentrated in vacuo. The crude residue was triturated with hexane, filtered, and recrystallized from dichloromethane-methanol to afford the title compound as a homogeneous, white, crystalline solid (0.17 g, 73%), m.p. 195-200° C.;

Workup

  1. customthe reaction was quenched with a saturated, aqueous sodium bicarbonate solution (100 mL)
  2. extractionextracted with dichloromethane (6×20 mL)
  3. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe solvent concentrated in vacuo
  6. customThe crude residue was triturated with hexane
  7. filtrationfiltered
  8. customrecrystallized from dichloromethane-methanol

Sources & evidence

ORD record
ord-25d5eabb6e9a4173b28308f9a6e57ff7
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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