Water → HCID 67470499, 화합물

HRID 1522589

반응식

HRID 1522589 반응식
[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

참가 물질

7

반응물 4

HCID 962WaterHCID 10796Cesium carbonate3회HCID 2734443(R)-(+)-4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane3회HCID 67469559HCID 67469559, 화합물

생성물 1

HCID 67470499HCID 67470499, 화합물

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cdcc36c0edf04d7a9763e48de5f857ba
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073918B2

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