Benzene, 4-bromo-1,2-dimethoxy- → tert-butyl (2R)-4-(3,4-dimethoxyphenyl)-2-propan-2-ylpiperazine-1-carboxylate

HRID 716

Reaktionsgleichung

Reaktionsgleichung von HRID 716
CC(C)[C@@H]1CNCCN1C(=O)OC(C)(C)C.COc1ccc(Br)cc1OC>CC(C)(C)[O-].CN(C)c1ccccc1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd]>COc1ccc(N2CCN(C(=O)OC(C)(C)C)[C@H](C(C)C)C2)cc1OC

Komponenten

7

Edukt 2

HCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 24820392(R)-1-Boc-2-isopropylpiperazine

Produkt 1

HCID 69098812tert-butyl (2R)-4-(3,4-dimethoxyphenyl)-2-propan-2-ylpiperazine-1-carboxylateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23676156Sodium t-butoxideReagenzHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylKatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

21-Apr-09 08:58:54 +0100 4-bromo-1,2-dimethoxybenzene (0.135 mL, 0.92 mmol), (R)-tert-butyl 2-isopropylpiperazine-1-carboxylate (252 mg, 1.11 mmol) and 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl (10.88 mg, 0.03 mmol) and Sodium tert-butoxide (128 mg, 1.29 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (21.09 mg, 0.02 mmol) were suspended in toluene (5 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. LC-MS show sproduct at 60% and SM 33% reaction mixture to be combined with EN02263-45 and worked up.

Quellen und Nachweise

ORD-Eintrag
ord-8ac590d4cc01454e9f3c19a34317cb92
Quelldatensatz
750 AstraZeneca ELN dataset
Originallink
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