Hydrochloric Acid → HCID 22482290, compound

HRID 2181858Notes

Reaction equation

HRID 2181858 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[N:12]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:11]([CH2:27][CH3:28])[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([F:29])[CH:9]=3)[C:4]=2[CH:3]=1.[CH2:30]([Li])CCC.CCCCCC.IC.Cl.[Cl-].[Na+]>O1CCCC1>[CH2:27]([CH:11]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([F:29])[CH:9]=2)[C:4]2[CH:3]=[C:2]([CH3:30])[CH:15]=[CH:14][C:13]=2[N:12]1[S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH3:28]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 8058HexaneHCID 224823412-Bromo-6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridineHCID 178418339Butyllithium

Product 1

HCID 22482290HCID 22482290, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 2-bromo-6-ethyl-8-fluoro-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (Example 44, Step c, 0.30 g, 0.63 mmol) in tetrahydrofuran (7 mL) was cooled to −78° C., and treated drop-wise under nitrogen with a solution of 1.4 M n-butyllithium in hexane (0.9 mL, 1.26 mmol). After stirring for 10 min, iodomethane (0.08 mL, 1.26 mmol) was added, and the reaction stirred until room temperature was reached. The reaction was quenched with a 0.1 N hydrochloric acid solution (15 mL, 1.5 mmol), and a saturated, aqueous, sodium chloride solution (150 mL). The separated aqueous phase was extracted with diethyl ether (3×20 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to a crude product, which was used without further purification;

Workup

  1. stirringthe reaction stirred until room temperature
  2. extractionThe separated aqueous phase was extracted with diethyl ether (3×20 mL)
  3. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a crude product, which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-2680fce900154b13b7fef1f002b68145
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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