Chloromethyl Methyl Ether → N-(2-bromo-5-methyl-pyridin-3-yl)-4-chloro-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

HRID 1898111Notes

Reaction equation

HRID 1898111 reaction equation
[Br:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([CH3:23])=[CH:4][N:3]=1.[CH3:24][O:25][CH2:26]Cl.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[Br:1][C:2]1[C:7]([N:8]([CH2:24][O:25][CH3:26])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=2)(=[O:10])=[O:11])=[CH:6][C:5]([CH3:23])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 57942390N-(2-bromo-5-methyl-pyridin-3-yl)-4-chloro-3-trifluoromehtyl-benzenesulfonamide

Product 1

HCID 57942173N-(2-bromo-5-methyl-pyridin-3-yl)-4-chloro-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamideYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(2-bromo-5-methyl-pyridin-3-yl)-4-chloro-3-trifluoromethyl-benzenesulfonamide (1.4 g, 3.27 mmol), chloromethyl methyl ether (0.4 mL, 5.23 mmol) and K2CO3 (1.35 g, 9.81 mmol) in THF (20 mL) was stirred at room temperature for 3 h. The mixture was filtered and the filtrate was concentrated and purified by flash chromatography (SiO2, 20% EtOAc-hexanes) to afford N-(2-bromo-5-methyl-pyridin-3-yl)-4-chloro-N-methoxymethyl-3-trifluoromethyl-benz-enesulfonamide (1.3 g) as a white solid in 84% yield. ESMS m/z (relative intensity): 473 (M+H)+ (100).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. custompurified by flash chromatography (SiO2, 20% EtOAc-hexanes)

Sources & evidence

ORD record
ord-292236b383d44bc794deb44d02142395
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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