Water → HCID 67470499、化合物

HRID 1522589

反応式

HRID 1522589 の反応式
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[N:9][NH:10][C:3]=12.Cl[CH2:12][C@H:13]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:18][C:15]1([CH3:19])[O:14][C@@H:13]([CH2:12][N:10]2[C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[I:1])[CH:8]=[N:9]2)[CH2:17][O:16]1

参加物

7

反応物 4

HCID 962WaterHCID 10796Cesium carbonate3 回HCID 2734443(R)-(+)-4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane3 回HCID 67469559HCID 67469559、化合物

生成物 1

HCID 67470499HCID 67470499、化合物

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

7-Iodo-1H-pyrazolo[4,3-b]pyridine (50 mg, 0.204 mmol), (R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (30.7 mg, 0.204 mmol), and cesium carbonate (133 mg, 0.408 mmol) in DMF (1.0 mL) was heated in a microwave at 80° C. for 15 minutes. Additional (R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (61.4 mg, 0.204 mmol) and cesium carbonate (67 mg) was added the reaction was heated in microwave at 80° C. for 2 hour. Additional (R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (30.7 mg, 0.204 mmol), tetrabutylammonium iodide (301 mg, 0.816 mmol) and cesium carbonate (133 mg, 0.408 mmol) was added and the reaction was heated in microwave at 80° C. for 60 minutes, then the reaction was transferred to an oil bath and heating was continued overnight at 75° C. The reaction was cooled and poured into water (10 mL) and extracted with ethyl acetate (5 mL). The organic layer were dried over sodium sulfate, filtered, and concentrated to give (S)-1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-7-iodo-1H-pyrazolo[4,3-b]pyridine MS [M+H] found 360.2.

後処理

  1. temperaturethe reaction was heated in microwave at 80° C. for 60 minutes
  2. customthe reaction was transferred to an oil bath
  3. temperatureheating
  4. temperatureThe reaction was cooled
  5. extractionextracted with ethyl acetate (5 mL)
  6. dry with materialThe organic layer were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-cdcc36c0edf04d7a9763e48de5f857ba
出典データセット
uspto-grants-2015_07
特許番号
US09073918B2

関連ノート

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