Methanesulfonyl chloride → 5-Bromo-7-fluoro-1-(methylsulfonyl)indoline

HRID 2353460Notes

Reaction equation

HRID 2353460 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.[CH3:12][S:13](Cl)(=[O:15])=[O:14]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([S:13]([CH3:12])(=[O:15])=[O:14])[CH2:6][CH2:5]2

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 167926895-bromo-7-fluoro-2,3-dihydro-1H-indole

Product 1

HCID 684272595-Bromo-7-fluoro-1-(methylsulfonyl)indolineYield 66.6%

Procedure

This compound was prepared according to 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 methanesulfonyl chloride (0.15 mL, 1.94 mmol) to provide 5-bromo-7-fluoro-1-(methylsulfonyl)indoline (0.19 g). MS (ES) m/z 293.6; HPLC purity 98.4% at 210-370 nm, 8.4 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

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-9c7622cc82ac40c595c555a1cccdd2e5
Source dataset
uspto-grants-2010_07
Patent number
US07750038B2

Reaction notes

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