Pyridine → N-(5-bromo-2-fluoro-4-methoxyphenyl)ethanesulfonamide

HRID 518305Notes

Reaction equation

HRID 518305 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[Br:7][C:8]1[C:9]([O:16][CH3:17])=[CH:10][C:11]([F:15])=[C:12]([CH:14]=1)[NH2:13].N1C=CC=CC=1>C(Cl)Cl>[Br:7][C:8]1[C:9]([O:16][CH3:17])=[CH:10][C:11]([F:15])=[C:12]([NH:13][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 838222835-Bromo-2-fluoro-4-methoxyaniline

Product 1

HCID 118021927N-(5-bromo-2-fluoro-4-methoxyphenyl)ethanesulfonamideYield 73.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., ethansulfonylchloride (1.4 g, 10.9 mmol) was added dropwise to a solution of 5-bromo-2-fluoro-4-methoxyaniline (3.5 g, 24.0 mmol) in pyridine (1.3 g, 16.4 mmol) and dry CH2Cl2 (20 mL). After stirring at room temperature for 10 h, CH2Cl2 extractive work up and purification by silica gel chromatography (PE:EA=10:0 to 3:1) gave the title compound (2.5 g, 73.5%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.77 (d, J=8.4 Hz, 1H), 6.73 (d, J=11.6 Hz, 1H), 6.27 (s, 1H), 3.89 (s, 3H), 3.10 (q, J=7.6 Hz, 2H), 1.40 (t, J=7.6 Hz, 3H). LCMS: 334.0 (M+Na)+

Workup

  1. customCH2Cl2 extractive work up and purification by silica gel chromatography (PE:EA=10:0 to 3:1)

Sources & evidence

ORD record
ord-07e31b4743bb4b1daba7e388390d91f8
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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