Réaction #682749

ord-ddd8807406074a83991b30b4a5aef0ec

Équation de réaction

CNC(=O)c1c(I)oc2cc(N(C)S(C)(=O)=O)c(Br)cc12
5-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide
O=Cc1ccc(B(O)O)cc1
(4-formylphenyl)boronic acid
O=C([O-])[O-].[Na+].[Na+]
Na2CO3
→
CNC(=O)c1c(-c2ccc(C=O)cc2)oc2cc(N(C)S(C)(=O)=O)c(Br)cc12
5-bromo-2-(4-formylphenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide
Rendement 58.1%

Réactifs

CNC(=O)c1c(I)oc2cc(N(C)S(C)(=O)=O)c(Br)cc12
5-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide
O=Cc1ccc(B(O)O)cc1
(4-formylphenyl)boronic acid
O=C([O-])[O-].[Na+].[Na+]
Na2CO3

Réactifs

[Cl][Pd][Cl].[Fe+2].c1ccc(P(c2ccccc2)[c-]2cccc2)cc1.c1ccc(P(c2ccccc2)[c-]2cccc2)cc1
Pd(dppf)Cl2

Solvants

CN(C)C=O
DMF

Conditions de réaction

Température
100°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreAfter the solvent was removed
  2. 2
    Autrethe residue was purified by column chromatography (DCM:EtOAc=10:1)

Mode opératoire

To a degassed solution of compound 5-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (400 mg, 0.82 mmol), (4-formylphenyl)boronic acid (110 mg, 0.74 mmol) and Na2CO3 (174 mg, 1.6 mmol) in DMF (4 mL) was added Pd(dppf)Cl2 (20 mg) under N2, and the mixture was stirred at 100° C. for 2 h. After the solvent was removed, the residue was purified by column chromatography (DCM:EtOAc=10:1) to give the product of compound 5-bromo-2-(4-formylphenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (200 mg, yield: 52%). 1H-NMR (CDCl3, 400 MHz) 10.09 (s, 1H), 8.09˜8.15 (m, 3H), 8.02 (s, 2H), 7.75 (s, 1H), 5.90 (s, 1H), 3.36 (s, 3H), 3.11 (s, 3H), 3.05 (d, J=4.8 Hz, 3H). MS (M+H)+: 465/467.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09242998B2uspto-grants-2016_01