Water → 3-Fluoro-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

HRID 2181893Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

N-[1-(2′,4′-Difluoro-1,1′-biphenyl-2-yl)ethyl]4-methoxybenzenesulfonamide (347 mg, 0.86 mmol) was dissolved in anhydrous N,N-dimethylformamide (2 mL) and potassium carbonate (238 mg, 1.72 mmol) was added as a solid in one portion. The mixture was heated at 100° C. with stirring until a single product had formed as gauged by LCMS (5-6 hours). Water (10 mL) was added and a white solid precipitated from the cloudy solution. The mixture was allowed to stand until the solution was clear, and the precipitated solid was filtered and washed with additional water to afford the desired compound (324 mg, 98%) as a white solid, m.p. 137.5-139° C.;

Workup

customhad formed
customas gauged by LCMS (5-6 hours)
customa white solid precipitated from the cloudy solution
filtrationthe precipitated solid was filtered
washwashed with additional water

Sources & evidence

ORD record: ord-8f7a79e8c94445db8000f2092601fa74
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06894061B2

Reaction notes

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