Isopropyl iodide → HCID 9947363, compound

HRID 1815104Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([N:8]2[C:12]([OH:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[N:9]2)[CH:5]=[CH:4][C:3]=1[S:18]([NH2:21])(=[O:20])=[O:19].C(=O)([O-])[O-].[K+].[K+].[CH:28](I)([CH3:30])[CH3:29].[OH-].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[C:12]([O:13][CH:28]([CH3:30])[CH3:29])=[CH:11][C:10]([C:14]([F:16])([F:17])[F:15])=[N:9]2)[CH:5]=[CH:4][C:3]=1[S:18]([NH2:21])(=[O:19])=[O:20]

Participants

Conditions

Temperature: 50 °C

Procedure

2-Fluoro-4-(5-hydroxy-3-trifluoromethyl-pyrazol-1-yl)-benzenesulfonamide (163 mg) and potassium carbonate (276 mg) were mixed in dimethyl formamide, followed by the addition of isopropyl iodide. The reaction mixture was stirred at 50° C. for 1.5 hours. After cooling to room temperature, 0.5 N sodium hydroxide solution (10 ml) was added, and the product was extracted with ethyl acetate (50 ml) and benzene (25 ml). The organic layer was dried with sodium sulfate, and the solvent was evaporated in vacuo to give the crude product, which was purified by preparative silica gel plate using 5:2 of hexane:ethyl acetate to afford the title compound (32 mg). The title compound was characterized by tandem high pressure liquid chromatography/mass spectrometry and yielded a retention time of 7.523 minutes and had a parent ion at 368 AMU.

Workup

temperatureAfter cooling to room temperature
extractionthe product was extracted with ethyl acetate (50 ml) and benzene (25 ml)
dry with materialThe organic layer was dried with sodium sulfate
customthe solvent was evaporated in vacuo
customto give the crude product, which
customwas purified by preparative silica gel plate

Sources & evidence

ORD record: ord-fb97579b78aa49d5bf8ecf2ff5ca90ee
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878726B2

Reaction notes

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