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Potassium Phosphate, Tribasic → tert-butyl (3R)-3-({[3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl]carbonyl}amino)piperidine-1-carboxylate

HRID 1467338
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1467338
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([NH:13][C@@H:14]3[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]3)=[O:12])[CH:9]=2)[N:4]([C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[N:16]1[CH:17]=[CH:18][C:19]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]([NH:13][C@@H:14]4[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]4)=[O:12])[CH:9]=3)[N:4]([C:27]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:3]=2)=[CH:14][CH:15]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 62657Potassium Phosphate, TribasicHCID 70652333(R)-tert-butyl 3-(3-bromo-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate

Produkt 1

HCID 86681283tert-butyl (3R)-3-({[3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl]carbonyl}amino)piperidine-1-carboxylateAusbeute 190 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24290Palladium ChlorideKatalysator
HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Katalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A flask was charged with tert-butyl (3R)-3-{[(3-bromo-1-trityl-1H-indazol-5-yl)carbonyl]amino}piperidine-1-carboxylate (4.00 g, 6.01 mmoles), potassium phosphate (2.05 g, 9.66 mmoles) and 1,1′-Bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (160.0 mg, 0.219 mmoles). The flask was put under an atmosphere of argon (3× vacuum/argon cycle) and degassed dioxane (20 mL) and water (5 mL) were injected. The reaction was heated to 80° C. for 16 hours and was then allowed to cool to ambient temperature. The resulting solution was poured into water (100 mL) and the aqueous emulsion was washed three times with chloroform/isopropanol (4:1, 50 mL portions). The combined organic washings were dried over sodium sulfate, filtered and concentrated to dryness. Flash chromatography (gradient 0-15% dichloromethane/methanol) to yield tert-butyl (3R)-3-({[3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl]carbonyl}amino)piperidine-1-carboxylate as a white solid (3.79 g, 95%).

Aufarbeitung

  1. customdegassed dioxane (20 mL) and water (5 mL)
  2. temperatureto cool to ambient temperature
  3. additionThe resulting solution was poured into water (100 mL)
  4. washthe aqueous emulsion was washed three times with chloroform/isopropanol (4:1, 50 mL portions)
  5. dry with materialThe combined organic washings were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-702c3980382f4b7c952dc961ee692bb5
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08999957B2

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