4-Methoxybenzenesulfonyl chloride → (S)-8-Fluoro-5-(4-methoxy-benzenesulfonyl)-6-methyl-5,6-dihydrophenanthridine

HRID 2224627Notes

Reaction equation

HRID 2224627 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([CH3:16])[N:6]=[C:7]3[C:12]=2[CH:11]=[CH:10][CH:9]=[CH:8]3)[CH:3]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.B.CSC.B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.[OH-].[Na+]>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:25]([C:22]1[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=1)(=[O:27])=[O:26])[C@H:5]2[CH3:16]

Participants

7

Reactant 5

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 12423031(Dimethyl sulfide)trihydroboronHCID 224823738-Fluoro-6-methylphenanthridine

Product 1

HCID 58597403(S)-8-Fluoro-5-(4-methoxy-benzenesulfonyl)-6-methyl-5,6-dihydrophenanthridineYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 8-fluoro-6-methylphenanthridine (0.5 g, 2.4 mmol) and 4-methoxybenzenesulfonyl chloride (0.514 g, 2.49 mmol) in dichloromethane (5 mL) was added to a solution of borane-methyl sulfide (0.142 mL, 1.42 mmol, 10 M solution in methyl sulfide) and (R)-2-methyl-CBS-oxazaborolidine (0.47 mL, 0.4734 mmol, 1.0 M solution in toluene) in dry dichloromethane (6 mL) over the course of three hours at room temperature. The reaction mixture was stirred for twelve hours and then a solution of aqueous sodium hydroxide (10 mL, 1 N) was added. The aqueous layer was extracted with dichloromethane (3×). The organic layers were combined, washed with a solution of saturated, aqueous sodium chloride, and dried over anhydrous sodium sulfate. The organic solvent was removed in vacuo to yield the crude product as an orange solid. The crude product was purified by chromatography on silica gel (1:10 ethyl acetate:hexane) to afford the title compound as a white solid (0.489 g, 1.28 mmol, 54% ).

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane (3×)
  2. washwashed with a solution of saturated, aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe organic solvent was removed in vacuo
  5. customto yield the crude product as an orange solid
  6. customThe crude product was purified by chromatography on silica gel (1:10 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-029fac92e1e044278c10f1d5b032ee8a
Source dataset
uspto-grants-2008_05
Patent number
US07378427B2

Reaction notes

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