Acetic Acid → HCID 178489372, 화합물

HRID 272041

반응식

HRID 272041 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[N:9][N:8](COCC[Si](C)(C)C)[C:5]2=[N:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[N:9][NH:8][C:5]2=[N:6][CH:7]=1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 598360325-bromo-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine

생성물 1

HCID 178489372HCID 178489372, 화합물수율 97%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

To a solution of 5-bromo-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine (260 mg, 0.60 mmol) in THF (3 mL) was added tetrabutylammonium fluoride (6 mL of 1 M in THF solution, 6.00 mmol) and molecular sieves. The solution was heated under reflux (70° C.) for 4 hours without stirring. The solution was cooled to ambient temperature and acidified to pH=5 by adding dropwise a dilute solution of acetic acid in MeOH. The solution was filtered and the filtrate was concentrated via rotary evaporation. The material was extracted into EtOAc and washed 3× H2O. The organic layer was dried over Na2SO4 and concentrated down to afford 5-bromo-3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridine as an orange solid (177 mg, 97% yield).

후처리

  1. temperatureThe solution was heated
  2. temperatureThe solution was cooled to ambient temperature
  3. filtrationThe solution was filtered
  4. concentrationthe filtrate was concentrated via rotary evaporation
  5. extractionThe material was extracted into EtOAc
  6. washwashed 3× H2O
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated down

출처 및 근거

ORD 기록
ord-fd570d53722f4c7497af126a80a45b49
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452993B2

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