Methyl iodide → 5-bromo-2-(6-(4-fluorophenoxy)pyridin-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595565Notes

Reaction equation

HRID 595565 reaction equation
[Br:1][C:2]1[C:3]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[N:12][C:13]([O:16][C:17]4[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=4)=[CH:14][CH:15]=3)=[C:7]([C:24]([NH:26][CH3:27])=[O:25])[C:6]=2[CH:28]=1.[C:34]([O-])([O-])=O.[K+].[K+].CI>CS(C)=O.O>[Br:1][C:2]1[C:3]([N:29]([CH3:34])[S:30]([CH3:33])(=[O:31])=[O:32])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[N:12][C:13]([O:16][C:17]4[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=4)=[CH:14][CH:15]=3)=[C:7]([C:24]([NH:26][CH3:27])=[O:25])[C:6]=2[CH:28]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 903324665-bromo-2-(6-(4-fluorophenoxy)pyridin-3-yl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide

Product 1

HCID 903324065-bromo-2-(6-(4-fluorophenoxy)pyridin-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamideYield 20%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a degassed solution of 5-bromo-2-(6-(4-fluorophenoxy)pyridin-3-yl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (100 mg, 0.187 mmol) and K2CO3 (53 mg, 0.374 mmol) in DMSO (2 mL) was added MeI (27 mg, 0.187 mmol) under N2. The mixture was heated at 20° C. for 2 h. The reaction mixture was diluted with H2O and extracted with EtOAc. It was washed with H2O, brine and dried over Na2SO4. After concentrated, the residue was purified by column chromatography (PE:EA=2:1) to give the product of 5-bromo-2-(6-(4-fluorophenoxy)pyridin-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (20 mg, yield: 20%). 1H-NMR (CDCl3, 400 MHz) δ 8.63 (d, J=2.8 Hz, 1H), 8.21˜8.24 (m, 1H), 8.02 (s, 1H), 7.65 (s, 1H), 7.06˜7.08 (m, 3H), 6.98 (d, J=8.8 Hz, 1H), 5.77 (d, J=8.8 Hz, 1H), 3.27 (s, 3H), 3.03 (s, 3H), 2.96 (d, J=4.8 Hz, 3H). MS (M+H)+: 548/550.

Workup

  1. extractionextracted with EtOAc
  2. washIt was washed with H2O, brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentrated
  5. customthe residue was purified by column chromatography (PE:EA=2:1)

Sources & evidence

ORD record
ord-ffdb5905509b4e5a9489c10f1ab4e0d3
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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