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

HRID 595705노트

반응식

HRID 595705 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-44594b247883409db9d9be62545d1b63
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243002B2

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