1-Propanesulfonyl chloride → HCID 68426924, compound

HRID 2353457Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.[CH2:11]([S:14](Cl)(=[O:16])=[O:15])[CH2:12][CH3:13]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:14]([CH2:11][CH2:12][CH3:13])(=[O:16])=[O:15])[CH2:6][CH2:5]2

Participants

Reactant 2

HCID 662791-Propanesulfonyl chloride

HCID 34115665-Bromoindoline

Product 1

HCID 68426924HCID 68426924, compoundYield 52.6%

Procedure

This compound was prepared using the general procedure for sulfonylation of indolines and tetrahydroquinolines as described in Example 4 using 5-bromoindoline (0.396 g, 2.0 mmol) and propylsulfonyl chloride (0.34 mL, 3 mmol) to provide 5-bromo-1-(propylsulfonyl)indoline (0.32 g). MS (ES) m/z 303.6; HPLC purity 100.0% at 210-370 nm, 9.8 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammonium formate buffer pH=3.5 acetonitrile+MeOH) for 10 minutes, hold 4 minutes.

Workup

customThis compound was prepared

Sources & evidence

ORD record: ord-215132909f5d4335b33501f2b384b527
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750038B2

Reaction notes

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