8-{4-Fluoro-3-[2-(4-methanesulfonyl-phenyl)-vinyl]-phenyl}-6-isopropyl-quinoline → 8-{4-Fluoro-3-[2-(4-methanesulfonyl-phenyl)-ethyl]-phenyl}-6-isopropyl-quinoline

HRID 896702Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:18]([CH3:20])[CH3:19])[CH:11]=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)=[CH:4][C:3]=1[CH:21]=[CH:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:18]([CH3:19])[CH3:20])[CH:11]=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)=[CH:4][C:3]=1[CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 8-{4-fluoro-3-[2-(4-methanesulfonyl-phenyl)-vinyl]-phenyl}-6-isopropyl-quinoline from Step 4 (200 mg, 0.45 mmol) and polymer supported phenylsulfonyl hydrazide (1.0 g) in toluene (10 mL) was heated at 100° C. for 18 h. The resulting mixture was cooled at 21° C., filtered and the solvent evaporated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 70:30 to 40:60) provided the 8-{4-fluoro-3-[2-(4-methanesulfonyl-phenyl)-ethyl]-phenyl}-6-isopropyl-quinoline compound.

Workup

temperatureThe resulting mixture was cooled at 21° C.
filtrationfiltered
customthe solvent evaporated
customPurification
washby flash chromatography (eluting with hexane/ethyl acetate, 70:30 to 40:60)

Sources & evidence

ORD record: ord-f221f057077740c38000d48e1a03ddaa
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919353B2

Reaction notes

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