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

HRID 595665Notes

Reaction equation

HRID 595665 reaction equation
[Br:1][C:2]1[C:3]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])=[CH:4][C:5]2[O:9][C:8]([C:10](N(OC)C)=[O:11])=[C:7]([C:16]([NH:18][CH3:19])=[O:17])[C:6]=2[CH:20]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[Br:1][C:2]1[C:3]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:23])=[O:24])=[CH:4][C:5]2[O:9][C:8]([CH:10]=[O:11])=[C:7]([C:16]([NH:18][CH3:19])=[O:17])[C:6]=2[CH:20]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 903324825-bromo-N2-methoxy-N2,N3-dimethyl-6-(N-methylmethylsulfonamido)benzofuran-2,3-dicarboxamide

Product 1

HCID 903324905-bromo-2-formyl-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamideYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

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.

Workup

  1. customThen it was quenched with HCl (a.q.)
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fbf5b94602bd4a62b73517bbea06dbb1
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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