Diisobutylaluminum hydride → 5-bromo-2-formyl-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

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Reaction Conditions

Reaction Steps

To a mixture of 5-bromo-N2-methoxy-N2,N3-dimethyl-6-(N-methylmethylsulfonamido)benzofuran-2,3-dicarboxamide (1 g, 2.3 mmol) in THF (10 mL) was added DIBAL-H (11.5 mL, 11.5 mmol) at −78° C. dropwise. The mixture was stirred at −15° C. for 2 h. Then it was quenched with HCl (a.q.), extracted with CH2Cl2, dried over Na2SO4, concentrated. The residue was crude product of 5-bromo-2-formyl-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (700 mg, yield: 74%). 1H-NMR (CDCl3, 400 MHz) δ 10.07 (s, 1H), 9.14 (br s, 1H), 9.00 (s, 1H), 7.80 (s, 1H), 3.35 (s, 3H), 3.10 (s, 3H), 3.05 (d, J=4.4 Hz, 3H). MS (M+H)+: 389/391.

Provenance & Evidence