Water → 7-Phenylsulfonyl-1-(2-pyridyl)-3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindazole

HRID 2084285Notes

Reaction equation

[OH:1]OS([O-])=O.[K+].[C:7]1([S:13][CH:14]2[C:22]3[N:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[N:20]=[C:19]([CH3:29])[C:18]=3[C:17](=[O:30])[CH2:16][C:15]2([CH3:32])[CH3:31])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH2:33]>CO>[C:7]1([S:13]([CH:14]2[C:22]3[N:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[N:20]=[C:19]([CH3:29])[C:18]=3[C:17](=[O:30])[CH2:16][C:15]2([CH3:32])[CH3:31])(=[O:1])=[O:33])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of Oxone (2 g, 3.2 mmol) in 6 ml of water was added dropwise to a solution of 7-phenylthio-1-(2-pyridyl)-3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydroindazole (0.24 g, 0.66 mmol), prepared as described in example 8, in methanol (6 ml), maintained under stirring at 0° C. After the addition was complete, the reaction mixture was allowed to warm to room temperature and stirring was continued for about 1.5 hours. Water was then added and the mixture was extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate end evaporated. The residue was chromatographed on silica gel (cyclohexane:ethyl acetate=7:3), to yield the title compound as a colourless solid (0.175 g, 61%): m.p. 165-166° C.

Workup

customprepared
temperaturemaintained
additionAfter the addition
temperatureto warm to room temperature
stirringstirring
extractionthe mixture was extracted with dichloromethane
washThe combined organic layers were washed with brine
dry with materialdried over sodium sulfate end
customevaporated
customThe residue was chromatographed on silica gel (cyclohexane:ethyl acetate=7:3)

Sources & evidence

ORD record: ord-08004909ee314e15a60bc0fd731ae6f0
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716856B1

Reaction notes

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