Water → 3-(5-(difluoromethoxy)-3-iodo-1H-indazol-1-yl)-N,N-dimethylpropan-1-amine

HRID 246700

反応式

HRID 246700 の反応式
[F:1][CH:2]([F:14])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[I:13].C([O-])([O-])=O.[K+].[K+].Cl[CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26].O>CN(C=O)C>[F:14][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[N:8]=[C:7]2[I:13]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 178506407HCID 178506407、化合物

生成物 1

HCID 712798163-(5-(difluoromethoxy)-3-iodo-1H-indazol-1-yl)-N,N-dimethylpropan-1-amine収率 87%

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 solution of 5-(difluoromethoxy)-3-iodo-1H-indazole (1 g, 3.2 mmol) in DMF (25 mL) was added K2CO3 (1.8 g, 12.8 mmol) and 3-chloro-N,N-dimethylpropan-1-amine (1.1 g, 6.4 mmol), after the addition, the reaction mixture was stirred at 80° C. for 4 hour. After cooling to room temperature, H2O (25 mL) was added and product extracted with ethyl acetate (100 mL). The organic layer was washed with H2O (100 mL), brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure, the residue was purified by column chromatography (silica gel, 200-300 mesh, eluting with dichloromethane/CH3OH=10:1) to give 3-(5-(difluoromethoxy)-3-iodo-1H-indazol-1-yl)-N,N-dimethylpropan-1-amine (1.1 g, 78.5%) as yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.46-7.42 (m, 1H), 7.27-7.17 (m, 2H), 6.87-6.29 (t, 1H, J=73.8 Hz), 4.47-4.41 (m, 2H), 2.24-2.18 (m, 8H), 2.08-2.03 (m, 2H). LCMS: (M+H)+=396.

後処理

  1. additionafter the addition
  2. temperatureAfter cooling to room temperature
  3. extractionproduct extracted with ethyl acetate (100 mL)
  4. washThe organic layer was washed with H2O (100 mL), brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by column chromatography (silica gel, 200-300 mesh, eluting with dichloromethane/CH3OH=10:1)

出典と根拠

ORDレコード
ord-e04eea713074407a9aa54e2b01a1b2be
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

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