Acetonitrile → 1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile

HRID 2203350ノート

反応式

HRID 2203350 の反応式
C(#N)C.[NH:4]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[C:6]([C:13]#[N:14])=[N:5]1.C(=O)([O-])[O-].[K+].[K+].[F:21][C:22]([F:30])([F:29])[C:23]([F:28])([F:27])[CH2:24][CH2:25]I>CCOC(C)=O>[F:27][C:23]([F:28])([C:22]([F:30])([F:29])[F:21])[CH2:24][CH2:25][N:4]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[C:6]([C:13]#[N:14])=[N:5]1

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 1100921,1,1,2,2-Pentafluoro-4-iodobutaneHCID 178510690HCID 178510690、化合物

生成物 1

HCID 866789821-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
75 °C

実験手順

An acetonitrile solution (150 mL) containing the intermediate from Step C above (10.5 g, 43.7 mmol), potassium carbonate (30.2 g, 219 mmol) and 1,1,1,2,2-pentafluoro-4-iodobutane (23.95 g, 87 mmol) was heated at 75° C. for 48 hours. The reaction solution was cooled to room temperature and diluted with EtOAc. The solution was washed with water, brine and concentrated in vacuo. The residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the title compound. 1H NMR (400 MHz, CH3CN-d3): δ 8.71 (dd, J=4.47, 1.51 Hz, 1H); 8.31 (dd, J=8.22, 1.52 Hz, 1H); 7.44 (dd, J=8.24, 4.48 Hz, 1H); 4.92 (t, J=6.98 Hz, 3H); 3.00-2.82 (m, 2H). m/z=291.0 (M+H).

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. washThe solution was washed with water, brine
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-0b9bc2d444314247a59829f642c0b6e9
出典データセット
uspto-grants-2016_06
特許番号
US09365574B2

反応ノート

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