Methanesulfonyl chloride → 6-Bromo-1-(methylsulfonyl)-1,2,3,4-tetrahydroquinoline

HRID 2353463Notes

Reaction equation

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

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 47150296-Bromo-1,2,3,4-tetrahydroquinoline

Product 1

HCID 15110356-Bromo-1-(methylsulfonyl)-1,2,3,4-tetrahydroquinolineYield 60.2%

Procedure

This compound was prepared according to the general procedure for sulfonylation of indolines and tetrahydroquinolines described in Example 4 using 6-bromo-1,2,3,4-tetrahydroquinoline (0.40 g, 1.89 mmol) and methanesulfonyl chloride (0.22 mL, 2.8 mmol) to provide 6-bromo-1-(methylsulfonyl)-1,2,3,4-tetrahydroquinoline (0.33 g). MS (ES) m/z 289.7; HPLC purity 97.2% at 210-370 nm, 10.2 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-1feeb9d3ad38486c861236eb9d375f69
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750038B2

Reaction notes

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