Ethyl Acetate → tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 387547ノート

反応式

HRID 387547 の反応式
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[I:11][C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:19]=2[N:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[NH:14][N:13]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[I:11][C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:19]=2[N:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[N:14]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=2)[N:13]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 178452208HCID 178452208、化合物

生成物 1

HCID 68760648tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate収率 69.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

1-(Chloromethyl)-4-methoxybenzene (1 mL, 7.36 mmol) was slowly added to a stirring mixture of tert-butyl 4-(3-iodo-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (3.1 g, 6.134 mmol) and K2CO3 (1.27 g, 9.2 mmol) in DMF (30 mL) at room temperature. After 2 hours, EtOAc (200 mL) and water (100 mL) were added to the mixture, and the phases were separated with warming. The resulting organic suspension was washed with water (3×50 mL) with warming. Final organic phase was concentrated in vacuo without drying over MgSO4 to prevent the loss of the product. The residue was triturated with CH3CN, and the solid formed was filtered, washed with CH3CN (2×10 mL) and dried under high vacuum to provide tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (2.65 g, 69% yield) as a solid. LCMS (APCI+) m/z 626.1 (M+H)+, Retention time=4.96 minutes.

後処理

  1. customthe phases were separated
  2. temperaturewith warming
  3. washThe resulting organic suspension was washed with water (3×50 mL)
  4. temperaturewith warming
  5. concentrationFinal organic phase was concentrated in vacuo
  6. dry with materialwithout drying over MgSO4
  7. customThe residue was triturated with CH3CN
  8. customthe solid formed
  9. filtrationwas filtered
  10. washwashed with CH3CN (2×10 mL)
  11. customdried under high vacuum

出典と根拠

ORDレコード
ord-86d940b19736482e9fb71615f6ddfd1c
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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