Potassium Carbonate → 2-Fluoro-5-[(3-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

HRID 2181905Notes

Reaction equation

HRID 2181905 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][CH:24]=[C:23]([O:27][CH3:28])[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][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=3)(=[O:19])=[O:20])[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 22482356N-[1-(2',5'-Difluoro-1,1'-biphenyl-2-yl)ethyl]-3-methoxybenzenesulfonamide

Product 1

HCID 224823522-Fluoro-5-[(3-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridineYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from N-[1-(2′,5′-difluoro-1,1′-biphenyl-2-yl)ethyl]-3-methoxybenzenesulfonamide (440 mg, 1.1 mmol), anhydrous N,N-dimethylformamide (2 mL), and potassium carbonate (301 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 liquid 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 (100 mg, 24%) as a white solid;

Workup

  1. customThe product was purified by preparative liquid 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-054018f7db5644219ee8bf7ee0f8f58d
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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