1-Bromo-2-methylpropane → 4-fluoro-N-isobutyl-N-(6-methoxypyridin-2-yl)benzenesulfonamide

HRID 594106Notes

Reaction equation

HRID 594106 reaction equation
C(N=C(N(C)C)N(C)C)(C)(C)C.Br[CH2:14][CH:15]([CH3:17])[CH3:16].[F:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[N:30]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(#N)C>[F:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([N:28]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[N:30]=2)(=[O:27])=[O:26])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 898760604-fluoro-N-(6-methoxypyridin-2-yl)benzenesulfonamide

Product 1

HCID 898763574-fluoro-N-isobutyl-N-(6-methoxypyridin-2-yl)benzenesulfonamideYield 63.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (0.121 ml, 0.581 mmol), 1-bromo-2-methylpropane (0.126 ml, 1.162 mmol) and 4-fluoro-N-(6-methoxypyridin-2-yl)benzenesulfonamide (164 mg, 0.581 mmol) was prepared and dissolved in acetonitrile (4 mL). The reaction was heated by microwaves to 150° C. for 30 minutes, then again for a further 15 minutes. After cooling the reaction was quenched with sodium hydroxide in ethanol and concentrated in vacuo. The product was extracted to the organic phase of an acidic work up between ethyl acetate and 5% citric acid. The organic phase was dried by passing through a hydrophobic frit, concentrated in vacuo and purified by flash silica (Si) chromatography (0-25% ethyl acetate-cyclohexane gradient), to give the title compound (125.5 mg). LCMS (2 min, formic) Rt 1.33 min, m/z (ES+) 339 (M+H).

Workup

  1. customwas prepared
  2. temperatureAfter cooling the reaction
  3. customwas quenched with sodium hydroxide in ethanol
  4. concentrationconcentrated in vacuo
  5. extractionThe product was extracted to the organic phase of an acidic work up between ethyl acetate and 5% citric acid
  6. customThe organic phase was dried
  7. concentrationconcentrated in vacuo
  8. custompurified by flash silica (Si) chromatography (0-25% ethyl acetate-cyclohexane gradient)

Sources & evidence

ORD record
ord-3f58bd877713435fa7f3c4434428414a
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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