Dimethylformamide → 10-Chloro-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepine-2-carboxamide

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Reaktionsgleichung

[Cl:1][C:2]1[N:12]=[CH:11][C:10]2[O:9][CH2:8][CH2:7][N:6]3[CH:13]=[C:14](I)[N:15]=[C:5]3[C:4]=2[CH:3]=1.C[Si](C)(C)N[Si](C)(C)C.C[N:27](C)[CH:28]=[O:29]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[N:12]=[CH:11][C:10]2[O:9][CH2:8][CH2:7][N:6]3[CH:13]=[C:14]([C:28]([NH2:27])=[O:29])[N:15]=[C:5]3[C:4]=2[CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

A mixture of 10-chloro-2-iodo-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepine (2056 mg, 5.916 mmol), bis(triphenylphosphine)palladium(II) chloride (2.10E2 mg, 0.300 mmol) and hexamethyldisilazane (7.488 mL, 35.50 mmol) in 60 ml of N,N-Dimethylformamide was subjected to carbonylation at 1 atm with CO from balloon. The reaction mixture was heated at 70° C. for 1 h. The mixture was concentrated in vacuum, the residue partitioned between ethyl acetate and 1 M aqueous sodium carbonate. The organic extracts were washed with water, brine, dried over magnesium sulfate, concentrated in vacuum and purified on a 12 g silica column eluting with 0-5% MeOH in DCM to give 1300 mg (83%). MS (ESI+): 265.0. 1H NMR (500 MHz, DMSO) δ 8.37 (s, 1H), 8.22 (s, 1H), 7.93 (s, 1H), 7.70 (s, 1H), 7.25 (s, 1H), 4.56 (s, 4H).

Aufarbeitung

concentrationThe mixture was concentrated in vacuum
customthe residue partitioned between ethyl acetate and 1 M aqueous sodium carbonate
washThe organic extracts were washed with water, brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuum
custompurified on a 12 g silica column
washeluting with 0-5% MeOH in DCM
customto give 1300 mg (83%)

Quellen und Nachweise

ORD-Eintrag: ord-fa7448fa5ff948d49a22c47357d3f1a9
Quelldatensatz: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08242104B2

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