Iodine → HCID 178452208、化合物

HRID 387546ノート

反応式

HRID 387546 の反応式
[C:1]1([C:7]2[C:8]([N:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)=[C:9]3[CH:15]=[N:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[I:31]I>CN(C=O)C.CCOC(C)=O>[I:31][C:15]1[C:9]2[C:10](=[N:11][CH:12]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]=2[N:16]2[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20][CH2:21]2)[NH:13][N:14]=1

参加物

6

反応物 3

HCID 807Iodine2 回HCID 14797Potassium Hydroxide2 回HCID 68758199tert-butyl 4-(5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

生成物 1

HCID 178452208HCID 178452208、化合物収率 79.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

A mixture of tert-butyl 4-(5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (3 g, 7.75 mmol) and powdered potassium hydroxide (1.28 g, 19.4 mmol) in DMF (20 mL) was treated with iodine (3.93 g, 15.5 mmol), and the mixture was heated at 60° C. After 4 hours, the mixture was cooled to room temperature and treated with powdered KOH (700 mg, 10.7 mmol) and I2 (1.97 g, 7.75 mmol). The mixture was stirred at 60° C. for 1 hour. The mixture was cooled to room temperature, diluted with EtOAc (200 mL) and successively washed with saturated Na2S2O3 solution (2×20 mL) and water (2×50 mL). The organic layer was separated, dried (MgSO4), filtered, and concentrated in vacuo. The residue obtained was crystallized from boiling CH3CN to provide tert-butyl 4-(3-iodo-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (3.12 g, 79.7% yield) as a solid. LCMS (APCI+) m/z 506 (M+H)+, Retention time=4.04 minutes.

後処理

  1. temperaturethe mixture was cooled to room temperature
  2. temperatureThe mixture was cooled to room temperature
  3. washsuccessively washed with saturated Na2S2O3 solution (2×20 mL) and water (2×50 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue obtained
  9. customwas crystallized

出典と根拠

ORDレコード
ord-010555df074341a89e8b092d643d1dbc
出典データセット
uspto-grants-2013_02
特許番号
US08372842B2

反応ノート

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