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

HRID 75984Notes

Reaction equation

HRID 75984 reaction equation
[Br:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([Cl:22])=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:29][O:30][CH2:31]Cl>C1COCC1>[Br:1][C:2]1[C:7]([N:8]([CH2:29][O:30][CH3:31])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:19])([CH3:21])[CH3:20])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([Cl:22])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 57942597N-(2-bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-benzenesulfonamide

Product 1

HCID 57942088N-(2-bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-N-methoxymethyl-benzenesulfonamideYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution N-(2-bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-benzenesulfonamide (12.0 g, 35.0 mmol) and K2CO3 (24.0 g, 170 mmol) in 80 mL anhydrous THF was added chloromethyl methyl ether (4.0 mL, 52.7 mmol). The resultant heterogeneous solution was stirred for 60 minutes at ambient temperature and the solids were subsequently removed via filtration. The filtrate was then removed in vacuo and the residue was dissolved in EtOAc. The organics were washed with saturated Na2CO3, dried over MgSO4, and evaporated in vacuo to generate a brownish oil. The oil was finally triturated with hexanes and the resultant solid filtered to produce the desired product as a light yellowish solid (11.5 g, 86% yield): MS (ES) M+H expected 447.0, found 447.0.

Workup

  1. customthe solids were subsequently removed via filtration
  2. customThe filtrate was then removed in vacuo
  3. dissolutionthe residue was dissolved in EtOAc
  4. washThe organics were washed with saturated Na2CO3
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe oil was finally triturated with hexanes
  8. filtrationthe resultant solid filtered

Sources & evidence

ORD record
ord-9c6dfc8325be41b49c4cd476c6920de5
Source dataset
uspto-grants-2014_09
Patent number
US08835468B2

Reaction notes

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