1-Bromo-2-methylpropane → N-(5-chloro-2-fluorophenyl)-N-isobutyl-4-vinylbenzenesulfonamide

Temperature

20 °C

To a solution of N-(5-chloro-2-fluorophenyl)-4-vinylbenzenesulfonamide (822 mg, 2.64 mmol) in acetonitrile (10 mL) stirred in air at 20° C., was added 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (903 mg, 5.27 mmol). The reaction mixture was stirred at 20° C. for 2 hours. 1-bromo-2-methylpropane (0.573 mL, 5.27 mmol) was then added and the reaction vessel sealed and heated by microwaves (Emrys Optimiser) to 150° C. for 30 minutes. After cooling, the reaction mixture was concentrated in vacuo and redissolved in ethyl acetate. The organic phase was washed with water (10 mL), dried using a hydrophobic frit and evaporated in vacuo to give the crude product as a yellow oil which solidified. The crude was purified by silica (Si) chromatography using a 0-50% ethyl acetate-cyclohexane gradient. The appropriate fractions were combined and evaporated in vacuo to give the required product, 824 mg as a colourless oil. LCMS [LCMS2] Rt 1.46 min, m/z (ES+) 368 (M+H).

1. customthe reaction vessel sealed
2. temperatureheated by microwaves (Emrys Optimiser) to 150° C. for 30 minutes
3. temperatureAfter cooling
4. concentrationthe reaction mixture was concentrated in vacuo
5. dissolutionredissolved in ethyl acetate
6. washThe organic phase was washed with water (10 mL)
7. customdried
8. customevaporated in vacuo
9. customto give the crude product as a yellow oil which
10. customThe crude was purified by silica (Si) chromatography
11. customevaporated in vacuo

ORD record

ord-323efef127344b6a935977e8f2bfb5e5

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428452B2