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tert-Butyl carbamate → tert-butyl N-(5-chloropyridazin-3-yl)carbamate

HRID 704
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 704
CC(C)(C)OC(N)=O.Clc1cnnc(Cl)c1>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>CC(C)(C)OC(=O)Nc1cc(Cl)cnn1
KomponentenReaktionsbedingungenVersuchsvorschriftQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 2

HCID 77922tert-Butyl carbamateHCID 199596873,5-Dichloropyridazine

Produkt 1

HCID 71118623tert-butyl N-(5-chloropyridazin-3-yl)carbamateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 10796Cesium carbonateReagenzHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
Katalysator
HCID 4144353Palladium (II) acetateKatalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

**_April 15 2016_** 3,5-dichloropyridazine (1 g, 6.71 mmol), tert-butyl carbamate (3.93 g, 33.56 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (0.583 g, 1.01 mmol), PdOAc2 (0.452 g, 2.01 mmol) and CS2CO3 (4.37 g, 13.43 mmol) in 1,4-dioxane (20 mL) was degassed through recharged with nitrogen, and was heated at 80 °C overnight. **_April 18 2016_** LCMS showed 23% of the precursor @ 0.55 min (no mass ionization) left on a 2-min basic run. GCMS showed no precursor and 94% of an unknown @ 6.90 min (whihc might be the desired product but not ionizable) on a 10-min run. The reaction was cooled to RT. The crude mixture was concentrated to givr a dark-brown gum. The dark-brown gum was dissolved in EtOAc, washed with water, and evaporated to give a brown solid. The brown solid was passed through a 10 g SiO2 flash column eluting with EtOAc, collected all of the eluent, and then evaporated to give a brown solid as the crude. The crude would be used in EN08121-59 without purification, assuming 100% yield.

Quellen und Nachweise

ORD-Eintrag
ord-5053ba4582cb4771951a27c38d53fae2
Quelldatensatz
750 AstraZeneca ELN dataset
Originallink
Quelle ansehen

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