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

HRID 2203372ノート

反応式

HRID 2203372 の反応式
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]#[N:11])=[N:2]1.Br[CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O.CCOC(C)=O>[F:16][C:15]([F:18])([F:17])[CH2:14][CH2:13][N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]#[N:11])=[N:2]1

参加物

7

反応物 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 27251143-Bromo-1,1,1-trifluoropropaneHCID 178510690HCID 178510690、化合物

生成物 1

HCID 866790091-(3,3,3-trifluoropropyl)-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

1H-pyrazolo[3,4-b]pyridine-3-carbonitrile, as described in Step C of Example 158 (30 g, 208 mmol), 3-bromo-1,1,1-trifluoropropane (44.5 mL, 416 mmol) and potassium carbonate (95 g, 687 mmol) were combined in a flask with acetonitrile (300 mL) and stirred at 40° C. After 5 h, the reaction was cooled to rt and EtOAc and water were added. The layers were separated and the aqueous layer was washed two times with EtOAc. The combined organics were dried (Na2SO4) and filtered. The solvent was removed under reduced pressure and the material was used without further purification. 1H NMR (500 MHz, DMSO-d6): δ 8.77 (d, J=4.50 Hz, 1H); 8.46 (d, J=8.23 Hz, 1H); 7.51 (dd, J=8.22, 4.47 Hz, 1H); 4.86 (t, J=6.66 Hz, 2H); 3.10-2.98 (m, 2H). m/z=241.1 (M+H).

後処理

  1. temperaturethe reaction was cooled to rt
  2. customThe layers were separated
  3. washthe aqueous layer was washed two times with EtOAc
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customthe material was used without further purification

出典と根拠

ORDレコード
ord-8b44b416171b4d22bfcd5e3a2199f24e
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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