Cesium carbonate → HCID 118114536, Verbindung

HRID 1050571Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1050571
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:16](=[O:23])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[NH2:17].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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]>[C:14]([C:8]1([C:5]2[CH:6]=[CH:7][C:2]([NH:17][C:16](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:3][CH:4]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)#[N:15]

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 658143784-(4-Bromophenyl)piperidine-4-carbonitrile

Produkt 1

HCID 118114536HCID 118114536, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

The mixture of 4-(4-bromophenyl)piperidine-4-carbonitrile (347, 520 mg, 1.96 mmol), tert-butyl carbamate (460 mg, 3.92 mmol), Pd2(dba)3 (180 mg, 0.20 mmol), XantPhos (350 mg, 0.60 mmol), fine-powder Cs2CO3 (1.96 g, 6.0 mmol) in 30 mL dioxane was degassed using N2 stream for 5 min and stirred in 115° C. bath in N2 atmosphere for overnight. It was cooled to RT, diluted with EtOAc 200 mL and filtered. The filtrate was concentrated in vacuo and subjected to silica flash column using 0 to 30% MeOH in DCM to afford tert-butyl 4-(4-cyanopiperidin-4-yl)phenylcarbamate (348, 230 mg, 39%).

Aufarbeitung

  1. customwas degassed
  2. customfor 5 min
  3. temperatureIt was cooled to RT
  4. additiondiluted with EtOAc 200 mL
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0a913e8f101340d6bdc6ad81549d2a00
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382246B2

Notizen zur Reaktion

Wird geladen…