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Trifluoroacetic acid → 2-(3-(1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)-2-methylbutanenitrile

HRID 1920848
ノート
印刷プレビュー

反応式

HRID 1920848 の反応式
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[N:19](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:20]=[CH:21][C:14]=23)[CH:8]=1)([CH2:5][CH3:6])[C:3]#[N:4].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[NH:19]1[C:15]2=[N:16][CH:17]=[CH:18][C:13]([C:9]3[CH:8]=[C:7]([C:2]([CH3:1])([CH2:5][CH3:6])[C:3]#[N:4])[CH:12]=[CH:11][CH:10]=3)=[C:14]2[CH:21]=[N:20]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57969705HCID 57969705、化合物

生成物 1

HCID 579696382-(3-(1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)-2-methylbutanenitrile収率 72.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

2-Methyl-2-(3-(1-trityl-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)butanenitrile (240 mg, 0.46 mmol) was dissolved in dichloromethane (10 ml) and cooled down in an ice-bath. Triethylsilane (2.5 ml) was added followed by trifluoroacetic acid (2.5 ml). The resulting mixture was stirred at 0° C. for 2 hours and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium carbonate. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the title compound as a white solid (92 mg, 70% yield).

後処理

  1. temperaturecooled down in an ice-bath
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica gel by flash column chromatography

出典と根拠

ORDレコード
ord-eed5c094c05947a3a72930e06bab3570
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08173635B2

反応ノート

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