1-Bromo-2-methylpropane → 4-fluoro-N-isobutyl-N-(5-isopropylpyridin-2-yl)benzenesulfonamide

HRID 594118Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:21](N=C(N(C)C)N(C)C)([CH3:24])([CH3:23])[CH3:22].BrCC(C)C>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:22][CH:21]([CH3:24])[CH3:23])[C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

4-fluoro-N-(5-isopropylpyridin-2-yl)benzenesulfonamide (400 mg, 1.359 mmol) was dissolved in acetonitrile (4 mL), 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (284 μL, 1.36 mmol) added and the mixture stirred for 20 minutes. 1-Bromo-2-methylpropane (296 μL, 2.72 mmol) was then added and the reaction vessel sealed and heated by microwaves to 150° C. for 1 hour. The reaction was cooled and concentrated in vacuo, then the crude product was extracted to the organic phase of an aqueous work up between ethyl acetate and water. The organic phase was passed through a hydrophobic frit, concentrated in vacuo and purified by mass directed autoprep (formic acid modifier) to give the title compound (117 mg). LCMS (2 min, formic) Rt 1.38 min, m/z (ES+) 351 (M+H).

Workup

customthe reaction vessel sealed
temperatureThe reaction was cooled
concentrationconcentrated in vacuo
extractionthe crude product was extracted to the organic phase of an aqueous work up between ethyl acetate and water
concentrationconcentrated in vacuo
custompurified by mass

Sources & evidence

ORD record: ord-4eff40853b694a468954a70c0604116c
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242972B2

Reaction notes

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