Ethanesulfonyl chloride → HCID 68425037, compound

HRID 2353465Notes

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

Participants

Reactant 2

HCID 11667Ethanesulfonyl chloride

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

Product 1

HCID 68425037HCID 68425037, compoundYield 36.5%

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 ethanesulfonyl chloride (0.26 mL, 2.8 mmol) to provide 6-bromo-1-(ethylsulfonyl)-1,2,3,4-tetrahydroquinoline (0.21 g). MS (ES) m/z 303.7; HPLC purity 94.8% at 210-370 nm, 9.6 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-d7fc095ea4284bac93dcb910ebe42ce2
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750038B2

Reaction notes

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