Allyltributylstannane → n-(1,1-Dimethylpropyl) 2-(2-propenyl)benzenesulfonamide

HRID 1159095Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]([CH3:16])([CH3:15])[CH2:13][CH3:14])(=[O:10])=[O:9].[CH2:17]([Sn](CCCC)(CCCC)CCCC)[CH:18]=[CH2:19]>CN(C)C=O.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>[CH3:15][C:12]([NH:11][S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH2:19][CH:18]=[CH2:17])(=[O:10])=[O:9])([CH3:16])[CH2:13][CH3:14]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 2-bromo-N-(1,1-dimethylpropyl)benzenesulfonamide (5.00 g, 16.3 mmol) in dimethylformamide (dry, N2-degassed, 20 mL) were added allyltribuylstannane (6.07 mL, 19.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (189 mg, 0.163 mmol). The mixture was heated at 110° C. for 15 h. The reaction was concentrated in vacuo and the residue was chromatographed (silica, 40% dichloromethane/hexanes to dichloromethane gradient) to provide N-(1,1-dimethylpropyl) 2-(2-propenyl)benzenesulfonamide (4.04 g, 92%) as an off-white solid: LCMS (neg. ion spectrum) m/z 266.

Workup

concentrationThe reaction was concentrated in vacuo
customthe residue was chromatographed (silica, 40% dichloromethane/hexanes to dichloromethane gradient)

Sources & evidence

ORD record: ord-f94a1c8e587942e9bdfbb0feeb8138d5
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812024B2

Reaction notes

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