Tetramethyltin → N-ethyl-N-methyl-6-(trimethylstannyl)pyridine-3-sulfonamide

HRID 2091559Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]([CH2:13][CH3:14])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:15][Sn:16](C)([CH3:18])[CH3:17]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:13]([N:11]([CH3:12])[S:8]([C:5]1[CH:6]=[N:7][C:2]([Sn:16]([CH3:18])([CH3:17])[CH3:15])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH3:14]

Participants

Conditions

Temperature: 90 °C

Procedure

6-chloro-N-ethyl-N-methylpyridine-3-sulfonamide (2.34 g, 10.0 mmol), tetramethyl tin (1.08 g, 10.00 mmol) and Pd(PPh3)4 (572 mg, 0.50 mmol) were mixed in dioxane (5 mL). After degassing, the mixture was heated to 90° C. At completion, the reaction was cooled to room temperature and concentrated. The residue was then flashed over alumina (20-100% chloroform/hexane eluent) to afford N-ethyl-N-methyl-6-(trimethylstannyl)pyridine-3-sulfonamide (1.46 g, 40% yield).

Workup

customAfter degassing
temperatureAt completion, the reaction was cooled to room temperature
concentrationconcentrated

Sources & evidence

ORD record: ord-adf4e7f36cb848e8b7d52849d1df7af4
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440652B2

Reaction notes

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