Acetic Acid → HCID 178489372、化合物

HRID 272041

反応式

HRID 272041 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 178489372HCID 178489372、化合物収率 97%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fd570d53722f4c7497af126a80a45b49
出典データセット
uspto-grants-2008_11
特許番号
US07452993B2

関連ノート

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