Potassium Iodide → 4-[6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-2-ethyl-2,5,5-trimethyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 2279119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2279119
[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[N:9]=[C:10]([CH3:11])[C:5]2=[C:4]([CH2:18]OS(C)(=O)=O)[CH:3]=1.[C:24]([O:28][C:29]([N:31]1[CH2:36][C:35]([CH3:38])([CH3:37])[NH:34][CH2:33][C:32]1([CH2:40][CH3:41])[CH3:39])=[O:30])([CH3:27])([CH3:26])[CH3:25].CCN(C(C)C)C(C)C.[I-].[K+]>C1COCC1.O>[C:24]([O:28][C:29]([N:31]1[CH2:36][C:35]([CH3:38])([CH3:37])[N:34]([CH2:18][C:4]2[CH:3]=[C:2]([Br:1])[N:7]=[C:6]3[N:8]([CH:12]4[CH2:17][CH2:16][CH2:15][CH2:14][O:13]4)[N:9]=[C:10]([CH3:11])[C:5]=23)[CH2:33][C:32]1([CH2:40][CH3:41])[CH3:39])=[O:30])([CH3:27])([CH3:26])[CH3:25]

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 900135322-Ethyl-2,5,5-trimethyl-piperazine-1-carboxylic acid tert-butyl esterHCID 90013581Methanesulfonic acid 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl ester

Produkt 1

HCID 900134844-[6-Bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl]-2-ethyl-2,5,5-trimethyl-piperazine-1-carboxylic acid tert-butyl esterAusbeute 41,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 130 mg of methanesulfonic acid 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl ester, 99 mg of 2-ethyl-2,5,5-trimethyl-piperazine-1-carboxylic acid tert-butyl ester, 0.11 ml of DIPEA and 5 mg of potassium iodide in 2 ml of dry THF was heated to 160° C. for 50 min in a microwave reactor. For workup the mixture was taken up in water and ethyl acetate, the phases were separated, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtrated and concentrated in vacuo and the resulting residue was purified by flash chromatography (silica, heptane/ethyl acetate). 75 mg (41%) of the title compound were obtained.

Aufarbeitung

  1. customethyl acetate, the phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customthe resulting residue was purified by flash chromatography (silica, heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-83e56100fdd74c8da199a1a6beb36591
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133181B2

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