Hydrochloric Acid → HCID 68507519, Verbindung

HRID 1715391

Reaktionsgleichung

Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:14])=[C:6]([CH:13]=1)[C:7]([NH:9][CH:10]1[CH2:12][CH2:11]1)=[O:8].[CH3:15][O:16][CH2:17]/[CH:18]=[CH:19]/B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[Na+].[Na+].Cl>CN(C=O)C.C(O)CC>[Cl:14][C:5]1[CH:4]=[CH:3][C:2]([CH:19]=[CH:18][CH2:17][O:16][CH3:15])=[CH:13][C:6]=1[C:7]([NH:9][CH:10]1[CH2:12][CH2:11]1)=[O:8]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

5-Bromo-2-chloro-N-cyclopropyl-benzamide (19.3 g, 70.5 mmol) was dissolved in a mixture of DMF (350 mL) and 1-propanol (210 mL). Pd(OAc)2(PPh3)3 (2.64 g, 3.53 mmol) was added. (E)-2-(3-Methoxypropenyl)4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15 mL, 70.5 mmol) was added through a syringe, and aq. 2M Na2CO3 (123 mL) was added. The mixture was stirred at 80° C. for 2 h, and allowed to cool to rt. Aq. 10% HCl was added carefully until a pH of 2 was reached. The solvents were partially removed under reduced pressure, and the residue was extracted with Et2O (3×). The combined org. extracts were washed with water and brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:2→1:1→EtOAc) yielded the title compound (12.7 g, 68%). LC-MS: tR=0.82 min; ES+: 266.17.

Aufarbeitung

temperatureto cool to rt
customThe solvents were partially removed under reduced pressure
extractionthe residue was extracted with Et2O (3×)
washextracts were washed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (EtOAc/heptane 1:2→1:1→EtOAc)

Quellen und Nachweise

ORD-Eintrag: ord-1a85f1401cbe4be7a7302f4adddee2b9
Quelldatensatz: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07799805B2

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