Ethanesulfonyl chloride → 5-Bromo-1-(ethylsulfonyl)-7-fluoroindoline

HRID 2353461Notes

Reaction equation

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

Participants

Reactant 2

HCID 11667Ethanesulfonyl chloride

HCID 167926895-bromo-7-fluoro-2,3-dihydro-1H-indole

Product 1

HCID 684261385-Bromo-1-(ethylsulfonyl)-7-fluoroindolineYield 60.2%

Procedure

This compound was prepared using the general procedure for sulfonylation of indolines and tetrahydroquinolines described in Example 4 using 5-bromo-7-fluoroindoline (0.21 g, 0.97 mmol) and ethanesulfonyl chloride (0.18 mL, 1.9 mmol) to provide 5-bromo-1-(ethylsulfonyl)-7-fluoroindoline (0.18 g). MS (ES) m/z 307.6; HPLC purity 98.4% at 210-370 nm, 9.0 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-b8bb5f5052b94d73a5b33c9dc62bd0b1
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750038B2

Reaction notes

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