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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
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HRID 595565 반응식
[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
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6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 679
Dimethyl Sulfoxide
용매
HCID 962Water용매

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온도
20 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ffdb5905509b4e5a9489c10f1ab4e0d3
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242998B2

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