5-bromo-2-(5-ethoxy-4-methyl-4,5-dihydroisoxazol-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide → 5-bromo-N-methyl-2-(4-methylisoxazol-3-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595669Notes

Reaction equation

HRID 595669 reaction equation
[Br:1][C:2]1[C:3]([N:24]([CH3:29])[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:14]([CH3:15])[CH:13](OCC)[O:12][N:11]=3)=[C:7]([C:19]([NH:21][CH3:22])=[O:20])[C:6]=2[CH:23]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Br:1][C:2]1[C:3]([N:24]([CH3:29])[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:4][C:5]2[O:9][C:8]([C:10]3[C:14]([CH3:15])=[CH:13][O:12][N:11]=3)=[C:7]([C:19]([NH:21][CH3:22])=[O:20])[C:6]=2[CH:23]=1

Participants

3

Reactant 1

HCID 903324215-bromo-2-(5-ethoxy-4-methyl-4,5-dihydroisoxazol-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Product 1

HCID 903324795-bromo-N-methyl-2-(4-methylisoxazol-3-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamideYield 90.4%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A mixture of 5-bromo-2-(5-ethoxy-4-methyl-4,5-dihydroisoxazol-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (50 mg, 0.10 mmol) in DCM/TFA (1 mL/2 mL) was stirred at reflux for 16 h. It was washed with water, brine, dried over Na2SO4, and concentrated. The residue was purified by prep-TLC (DCM:MeOH=20:1) to get 5-bromo-N-methyl-2-(4-methylisoxazol-3-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (40 mg, yield: 88%). 1H-NMR (CDCl3, 400 MHz) δ 9.14 (br s, 1H), 8.84 (s, 1H), 8.39 (s, 1H), 7.76 (s, 1H), 3.35 (s, 3H), 3.10 (s, 3H), 3.04 (d, J=4.8 Hz, 3H), 2.36 (s, 3H). MS (M+H)+: 442/444.

Workup

  1. temperatureat reflux for 16 h
  2. washIt was washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by prep-TLC (DCM:MeOH=20:1)

Sources & evidence

ORD record
ord-079e266f986e4ca98c71f9b90be4427c
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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