Dichloromethane → HCID 10317801, compound

HRID 2181823Notes

Reaction equation

HRID 2181823 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)=[C:21]([CH3:27])[CH:20]=1)(=[O:18])=[O:17])[CH:5]2[CH3:28].B(Cl)(Cl)Cl.ClCCl.C(=O)(O)[O-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOCC.O>[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]([OH:25])=[C:21]([CH3:27])[CH:20]=1)(=[O:18])=[O:17])[CH:5]2[CH3:28]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 22482297HCID 22482297, compound

Product 1

HCID 10317801HCID 10317801, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 8-fluoro-5-[(4-methoxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine (0.30 g, 0.75 mmol) and tetrabutylammonium iodide (0.69 g, 1.9 mmol) was treated with 1 M boron trichloride in dichloromethane (1.9 mL, 1.9 mmol) at room temperature. After stirring for 24 hours at room temperature, the mixture was treated sequentially with water (20 mL), a saturated, aqueous, sodium bicarbonate solution (50 mL), and ether (20 mL). The separated aqueous phase was extracted with diethyl ether (3×25 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to a residue. The residue was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:4 to 3:7 gradient) to yield, the title compound as a homogeneous solid (0.21 g, 73%), m.p. 196° C.;

Workup

  1. extractionThe separated aqueous phase was extracted with diethyl ether (3×25 mL)
  2. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to a residue
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with a mixture of ethyl acetate-hexane (1:4 to 3:7 gradient)
  7. customto yield

Sources & evidence

ORD record
ord-c5fe98c163a745f7acb0c8e8a39cddfa
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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