Potassium Carbonate → N-{3-[4'-(2-Allyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-yl)-2-fluoro-biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

HRID 1446097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446097
[CH2:1]([C:4]1([C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)[O:8][C:7]2=[N:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][N:6]2[CH2:5]1)[CH:2]=[CH2:3].[F:22][C:23]1[CH:24]=[C:25]([N:38]2[CH2:42][CH:41]([CH2:43][NH:44][C:45](=[O:47])[CH3:46])[O:40][C:39]2=[O:48])[CH:26]=[CH:27][C:28]=1B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C.O>[CH2:1]([C:4]1([C:15]2[CH:20]=[CH:19][C:18]([C:28]3[CH:27]=[CH:26][C:25]([N:38]4[CH2:42][CH:41]([CH2:43][NH:44][C:45](=[O:47])[CH3:46])[O:40][C:39]4=[O:48])=[CH:24][C:23]=3[F:22])=[CH:17][CH:16]=2)[O:8][C:7]2=[N:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][N:6]2[CH2:5]1)[CH:2]=[CH2:3]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 22273985N-{3-[3-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamideHCID 442424052-Allyl-2-(4-bromo-phenyl)-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole

Produkt 1

HCID 68550437N-{3-[4'-(2-Allyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-yl)-2-fluoro-biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 21962138N,N-Dimethylformamide--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The title compound was synthesized according to the reaction scheme shown in FIG. 21. To a mixture of 2-Allyl-2-(4-bromo-phenyl)-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole (80 mg, 0.229 mmol), N-{3-[3-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (104 mg, 0.274 mmol), Pd(PPh3)4 (53 mg, 0.046 mmol) and K2CO3 (240 mg, 0.458 mmol) was added anhydrous DMF/H2O (4 mL/0.4 mL, 4.4 mL total) under N2. The reaction mixture was stirred for 2 h at 80° C., cooled to rt, quenched with water, diluted with EtOAc, washed with brine and water. The organic layers were separated, dried (MgSO4) and concentrated. Column chromatography provided 63 mg of yellow solid. 1H NMR (400 MHz, DMSO-d) δ 8.26 (t, J=5.8 Hz, 1H), 7.60 (m, 2H), 7.41 (m, 2H), 5.61 (m, 1H), 5.16 (m, 2H), 4.74 (m, 1H), 4.65 (d, J=11.2 Hz, 1H), 4.48 (d, J=11.2 Hz, 1H), 4.15 (d, J=9.0 Hz, 1H), 3.76 (m, 1H), 3.41 (d, J=1.3 Hz, 2H), 3.02 (m, 2H); ESI MS m/z 522 (M+H+)

Aufarbeitung

  1. customaccording to the reaction scheme
  2. temperaturecooled to rt
  3. customquenched with water
  4. additiondiluted with EtOAc
  5. washwashed with brine and water
  6. customThe organic layers were separated
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-48d04d8ccd824378a7257426930f11d8
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666864B2

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