Dimethylformamide → HCID 57742996, compound

HRID 1896369Notes

Reaction equation

I[C:2]1[C:3]([CH3:18])=[N:4][N:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[C:6]=1[CH3:7].C([Mg]Cl)(C)C.CN([CH:27]=[O:28])C>C1COCC1>[CH3:18][C:3]1[C:2]([CH:27]=[O:28])=[C:6]([CH3:7])[N:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[N:4]=1

Participants

Conditions

Temperature: -73 °C

Procedure

In a reaction vessel under inert atmosphere, 4-iodo-3,5-dimethyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole x53 (1.44 g, 3.8 mmol) is dissolved in dry THF (10 ml) and cooled down to −73° C. A 2M solution of isopropylmagnesiumchloride in THF (9.6 mmol, 4.8 ml) is added dropwise and the mixture is stirred at −73° C. for 1 h. Then 0.44 ml of DMF (5.7 mmol) are added and the solution stirred at room temperature overnight. DMF (1.9 mmol) is further added and stirring is continued for 16 h. The reaction mixture is quenched with a saturated solution of NH4Cl, extracted three times with CH2Cl2, the organic phase is washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give 0.88 g of crude 3,5-dimethyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrazole-4-carbaldehyde x56, which is used in the next step without any further purification.

Workup

stirringthe solution stirred at room temperature overnight
stirringstirring
waitis continued for 16 h
customThe reaction mixture is quenched with a saturated solution of NH4Cl
extractionextracted three times with CH2Cl2
washthe organic phase is washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b829896b45ff42a8b6ed26ba55b8b7f0
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518943B2

Reaction notes

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