Methyl iodide → 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-2H-indazole-3-carboxamide

HRID 595705ノート

反応式

HRID 595705 の反応式
[Br:1][C:2]1[C:10]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:9][C:8]2[C:4](=[C:5]([C:23]([NH:25][CH3:26])=[O:24])[N:6]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[N:7]=2)[CH:3]=1.[C:27]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[Br:1][C:2]1[C:10]([N:11]([CH3:27])[S:12]([CH3:15])(=[O:13])=[O:14])=[CH:9][C:8]2[C:4](=[C:5]([C:23]([NH:25][CH3:26])=[O:24])[N:6]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[N:7]=2)[CH:3]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 569631675-bromo-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)-2H-indazole-3-carboxamide

生成物 1

HCID 903324325-bromo-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-2H-indazole-3-carboxamide収率 95.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a suspension of 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)-2H-indazole-3-carboxamide (0.5 g, 1.1 mmol) and K2CO3 (0.5 g, 3.4 mmol) in DMF (10 mL) was added dropwise CH3I (0.8 g, 5.6 mmol) at 0° C. under N2, and then the mixture was stirred at 80° C. for 2 hours. After concentration under vacuum, the residue was suspended in H2O and extracted with DCM. The combined organic layer was washed with H2O, brine, dried over Na2SO4, filtrated and concentrated to give 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-2H-indazole-3-carboxamide (0.48 g, yield: 93%). 1H-NMR (CDCl3, 400 MHz) δ 8.21 (s, 1H), 8.01 (s, 1H), 7.56˜7.60 (m, 2H), 7.21˜7.27 (m, 2H), 6.97 (s, 1H), 3.228 (s, 3H), 3.07 (d, J=4.8 Hz, 3H), 2.77 (s, 3H). MS (M+H)+: 455/457.

後処理

  1. concentrationAfter concentration under vacuum
  2. extractionextracted with DCM
  3. washThe combined organic layer was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltrated
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-44594b247883409db9d9be62545d1b63
出典データセット
uspto-grants-2016_01
特許番号
US09243002B2

反応ノート

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