Potassium Carbonate → 2-Fluoro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

HRID 2181902Notes

Reaction equation

HRID 2181902 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]([NH:17][S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:8][C:5]1[CH:6]=[CH:7][C:2]2[N:17]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:15]([CH3:16])[C:10]3[C:9](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:3]=2[CH:4]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22482355N-[1-(2',5'-Difluoro-1,1'-biphenyl-2-yl)ethyl]-4-methoxybenzenesulfonamide

Product 1

HCID 224823152-Fluoro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridineYield 66.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from N-[1-(2′,5′-difluoro-1,1′-biphenyl-2-yl)ethyl]-4-methoxybenzenesulfonamide (450 mg, 1.1 mmol), anhydrous N,N-dimethylformamide (2 mL), and potassium carbonate (304 mg, 2.2 mmol) according to the procedure and in the same manner as described in Example 105, step d. The product was purified by preparative column chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g), eluting with a gradient of 30%-50% methyl tert-butyl ether in hexane (35 min), to afford the desired compound (280 mg, 65%) as a white solid, m.p. 167-168° C.;

Workup

  1. customThe product was purified by preparative column chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g)
  2. washeluting with a gradient of 30%-50% methyl tert-butyl ether in hexane (35 min)

Sources & evidence

ORD record
ord-207612d01d2345bc88d69c1015d25efe
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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