Cesium carbonate → tert-butyl 3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-ylcarbamate

HRID 1943890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943890
Br[C:2]1[CH:3]=[C:4]2[C:10]([O:11][CH3:12])=[N:9][N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:5]2=[N:6][CH:7]=1.[C:22](=[O:29])([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[NH2:23].C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:12][O:11][C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([NH:23][C:22](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:3]=2)[N:8]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:9]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 670888295-bromo-3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine

Produkt 1

HCID 67089104tert-butyl 3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-ylcarbamateAusbeute 24,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-Bromo-3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine (0.109 g, 0.313 mmol), tert-butyl carbamate (0.110 g, 0.939 mmol), Cs2CO3 (0.153 g, 0.470 mmol), Pd2 dba3*CHCl3 (0.0324 g, 0.0313 mmol) and 4,5-bis(diphenylphosphino)-9,9 dimethylxanthene (0.0362 g, 0.0626 mmol) were taken up in THF, degassed with argon for 15 minutes, and heated to reflux overnight. The solution was partitioned between water and EtOAc. The organic portion was washed with water (3×), brine, dried over Na2SO4 and concentrated to an oil which was purified by column chromatography (4:1 hexane/EtOAc) to give tert-butyl 3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-ylcarbamate (0.0298 g, 24.8%) as an oil.

Aufarbeitung

  1. customdegassed with argon for 15 minutes
  2. temperatureheated
  3. temperatureto reflux overnight
  4. customThe solution was partitioned between water and EtOAc
  5. washThe organic portion was washed with water (3×), brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to an oil which
  8. customwas purified by column chromatography (4:1 hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-4361c26ced224f75b46778539bcdbf7f
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394795B2

Notizen zur Reaktion

Wird geladen…