Lithium hydroxide, monohydrate → 5-bromo-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carboxylic acid

HRID 595663Notes

Reaction equation

HRID 595663 reaction equation
[Br:1][C:2]1[C:3]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12]C)=[O:11])=[C:7]([C:14](=[O:17])[NH:15][CH3:16])[C:6]=2[CH:18]=1.O[Li].O>O1CCOCC1.O>[Br:1][C:2]1[C:3]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:21])=[O:22])=[CH:4][C:5]2[O:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([C:14](=[O:17])[NH:15][CH3:16])[C:6]=2[CH:18]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 90332412methyl 5-bromo-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carboxylate

Product 1

HCID 903324625-bromo-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carboxylic acidYield 89.2%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a suspension of methyl 5-bromo-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carboxylate (2.90 g, 6.92 mmol) in 1,4-dioxane/H2O (30 mL/5 mL) was added LiOH.H2O (870 mg, 20.75 mmol). The mixture was stirred at room temperature overnight. Then it was concentrated in vacuo, diluted with water, acidized with HCl (aq. 2 M) and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated give the product of 5-bromo-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carboxylic acid (2.50 g, yield: 89%). It was used for the next step without further purification. 1H-NMR (DMSO-d6, 400 MHz) δ 9.16 (br s, 1H), 8.27 (s, 1H), 8.16 (s, 1H), 3.17 (s., 6H), 2.82 (d, J=4.4 Hz, 3H). (M+H)+: 405/407.

Workup

  1. concentrationThen it was concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0f916e70ca40490084764d5a1f34a10a
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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