Borane;tetrahydrofuran → 4-Isopropyl-N-[6-(1-propyl-azetidin-3-yl)-pyridin-3-yl]-benzenesulfonamide

HRID 2262617Notes

Reaction equation

HRID 2262617 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]([CH:20]3[CH2:23][N:22]([C:24](=O)[CH2:25][CH3:26])[CH2:21]3)=[CH:18][CH:19]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].B.C1COCC1>C1COCC1>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]([CH:20]3[CH2:23][N:22]([CH2:24][CH2:25][CH3:26])[CH2:21]3)=[CH:18][CH:19]=2)(=[O:11])=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 53628661HCID 53628661, compound

Product 1

HCID 536286604-Isopropyl-N-[6-(1-propyl-azetidin-3-yl)-pyridin-3-yl]-benzenesulfonamideYield 66.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-isopropyl-N-[6-(1-propionyl-azetidin-3-yl)-pyridin-3-yl]-benzenesulfonamide (150 mg, 0.38 mmol) in THF (15 ml) was added dropwise 1M BH3.THF (3.8 ml) and the mixture was stirred at room temperature for 12 h. It was then quenched by careful addition of 1N aqueous HCl (10 ml) and the resulting solution was heated at reflux for 4 h. The solution was next cooled to room temperature, adjusted to pH˜8 with 2 N NaOH solution and diluted with CH2Cl2. Separation of the layers, drying (Na2SO4) of the organic phase, filtration and evaporation in vacuo provided the crude material, which was purified by flash column chromatography (CH2Cl2:methanol, 95:5) to give the title compound (95 mg, 66%) as a light yellow oil.

Workup

  1. customIt was then quenched by careful addition of 1N aqueous HCl (10 ml)
  2. temperaturethe resulting solution was heated
  3. temperatureat reflux for 4 h
  4. temperaturenext cooled to room temperature
  5. additiondiluted with CH2Cl2
  6. customSeparation of the layers
  7. customdrying
  8. filtration(Na2SO4) of the organic phase, filtration and evaporation in vacuo
  9. customprovided the crude material, which
  10. customwas purified by flash column chromatography (CH2Cl2:methanol, 95:5)

Sources & evidence

ORD record
ord-6cfdb300404f43d5b39ca41edfc27498
Source dataset
uspto-grants-2010_12
Patent number
US07851463B2

Reaction notes

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