1-Bromo-3-methylbutane → 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isopentyl-N-(5-isopropylpyridin-2-yl)benzenesulfonamide

HRID 594164Notes

Reaction equation

HRID 594164 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][N:20]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[C:5]([CH3:28])[O:4][N:3]=1.C(N=C(N(C)C)N(C)C)(C)(C)C.Br[CH2:42][CH2:43][CH:44]([CH3:46])[CH3:45]>C(#N)C>[CH3:1][C:2]1[C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([S:15]([N:18]([CH2:42][CH2:43][CH:44]([CH3:46])[CH3:45])[C:19]3[CH:24]=[CH:23][C:22]([CH:25]([CH3:26])[CH3:27])=[CH:21][N:20]=3)(=[O:17])=[O:16])=[CH:13][CH:14]=2)=[C:5]([CH3:28])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 898760154-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(5-isopropylpyridin-2-yl)benzenesulfonamide

Product 1

HCID 721946914-((3,5-dimethylisoxazol-4-yl)methoxy)-N-isopentyl-N-(5-isopropylpyridin-2-yl)benzenesulfonamideYield 27.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 4-((3,5-dimethylisoxazol-4-yl)methoxy)-N-(5-isopropylpyridin-2-yl)benzenesulfonamide (150 mg, 0.37 mmol) in acetonitrile (4 mL) was added 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (128 mg, 0.75 mmol). The reaction mixture was stirred at 20° C. for 1 hour. 1-Bromo-3-methylbutane (0.09 mL, 0.75 mmol) was then added and the reaction vessel sealed and heated by microwaves to 150° C. for 30 minutes. The reaction mixture was concentrated in vacuo and diluted with ethyl acetate. The organic phase was washed with water, dried using a hydrophobic frit and evaporated in vacuo to give the crude product. The crude was then purified by flash silica (Si) chromatography (0-25% ethyl acetate-cyclohexane gradient). The appropriate fractions were combined and evaporated in vacuo to give the title compound (48 mg) as a yellow oil. LCMS (2 min, HpH) Rt 1.50 min, m/z (ES+) 472 (M+H).

Workup

  1. customthe reaction vessel sealed
  2. temperatureheated by microwaves to 150° C. for 30 minutes
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additiondiluted with ethyl acetate
  5. washThe organic phase was washed with water
  6. customdried
  7. customevaporated in vacuo
  8. customto give the crude product
  9. customThe crude was then purified by flash silica (Si) chromatography (0-25% ethyl acetate-cyclohexane gradient)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-6d5bfe80f5e349348e559bcd410ba2ae
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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