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

HRID 387581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387581
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+].CCOCC>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

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 178452208HCID 178452208, Verbindung

Produkt 1

HCID 68760648tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylateAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-(Chloromethyl)-4-methoxybenzene (0.128 mL, 0.938 mmol) was added to tert-butyl 4-(3-iodo-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.395 g, 0.782 mmol) and K2CO3 (0.130 g, 0.938 mmol) in DMF (10 mL). The reaction was stirred at room temperature for 2 hours. Ether (30 mL) and water (10 mL) were then added. The organic layer was separated, washed with brine, and dried over sodium sulfate. After removal of the solvent, the resulting residue was purified by column chromatography (hexane:ethyl acetate, 3:1) to give tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.33 g, 68%) as a solid. 1H NMR (400 Hz, CD2Cl2) δ 8.23 (s, 1H), 7.44 (m, 3H), 7.33 (d, J=8.8 Hz, 2H), 7.26 (m, 2H), 6.84 (d, J=8.8 Hz, 2H), 5.59 (s, 2H), 3.76 (s, 3H), 3.55 (m, 4H), 2.86 (m, 4H), 1.40 (s, 9H).

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe resulting residue was purified by column chromatography (hexane:ethyl acetate, 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-c61e0c95ed044d138f77c70dff932191
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372842B2

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