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

HRID 595565
ノート
印刷プレビュー

反応式

HRID 595565 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679
Dimethyl Sulfoxide
溶媒
HCID 962Water溶媒

反応条件

温度
20 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ffdb5905509b4e5a9489c10f1ab4e0d3
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242998B2

反応ノート

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