Ethanesulfonyl chloride → N-(2-(5-(2,3-dichlorophenyl)pyridin-3-yl)cyclopropyl)ethanesulfonamide

HRID 391350Notes

Reaction equation

HRID 391350 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([CH:15]2[CH2:17][CH:16]2[NH:18]C(=O)OCC2C=CC=CC=2)[CH:12]=[N:13][CH:14]=1.B(Br)(Br)Br.[CH2:33]([S:35](Cl)(=[O:37])=[O:36])[CH3:34].[NH4+].[Cl-]>C(Cl)Cl.O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([CH:15]2[CH2:17][CH:16]2[NH:18][S:35]([CH2:33][CH3:34])(=[O:37])=[O:36])[CH:12]=[N:13][CH:14]=1

Participants

7

Reactant 4

HCID 11667Ethanesulfonyl chlorideHCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 59578428Benzyl 2-(5-(2,3-dichlorophenyl)pyridin-3-yl)cyclopropylcarbamate

Product 1

HCID 49765870N-(2-(5-(2,3-dichlorophenyl)pyridin-3-yl)cyclopropyl)ethanesulfonamideYield 7.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of benzyl 2-(5-(2,3-dichlorophenyl)pyridin-3-yl)cyclopropylcarbamate (94 mg, 0.227 mmol) in DCM (3 ml) was added BBr3 (0.682 ml, 0.682 mmol) at 0° C. This reaction mixture was stirred for 1 h at 0° C. The reaction was quenched by addition of saturated NaHCO3 solution, and the mixture was extracted with AcOEt. The extract was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was dissolved in pyridine (3.00 ml), and ethanesulfonyl chloride (0.086 ml, 0.910 mmol) was added to the solution. This reaction mixture was stirred at room temperature. After 1 h, saturated NH4Cl solution in water was added. The mixture was extracted with AcOEt. The extract was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column (EtOAc/Heptane=0-50%, v/v) gave N-(2-(5-(2,3-dichlorophenyl)pyridin-3-yl)cyclopropyl)ethanesulfonamide (6.2 mg, 0.017 mmol, 7% yield). ESI-MS m/z: 371 [M+1]+. 1H NMR (CDCl3, 400 MHz) 1.31 (t, J=7.2 Hz, 3H), 1.38-1.43 (m, 2H), 2.35-2.38 (m, 1H), 2.86-2.91 (m, 1H), 3.14 (q, J=7.2 Hz, 2H), 7.41 (dd, J=7.6, 2.0 Hz, 1H), 7.47 (t, J=7.6 Hz, 1H), 7.57 (t, J=2.0 Hz, 1H), 7.65 (dd, J=7.6, 2.0 Hz, 1H), 8.46 (d, J=2.4 Hz, 1H), 8.53 (d, J=2.4 Hz, 1H).

Workup

  1. customThe reaction was quenched by addition of saturated NaHCO3 solution
  2. extractionthe mixture was extracted with AcOEt
  3. washThe extract was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in pyridine (3.00 ml)
  8. stirringThis reaction mixture was stirred at room temperature
  9. waitAfter 1 h
  10. extractionThe mixture was extracted with AcOEt
  11. washThe extract was washed with brine
  12. dry with materialdried over Na2SO4
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo
  15. customThe residue was purified by flash column (EtOAc/Heptane=0-50%, v/v)

Sources & evidence

ORD record
ord-62ec781f101549c18e13d33655d7ae47
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

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