Sodium Carbonate → HCID 67437737, Verbindung

HRID 2192457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192457
C([O-])([O-])=O.[Na+].[Na+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([C:24]2[C:28]3[CH:29]=[CH:30][C:31](B4OC(C)(C)C(C)(C)O4)=[CH:32][C:27]=3[S:26][N:25]=2)[CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:10][CH:9]=1.[N+:42]([C:45]1[CH:64]=[CH:63][C:48]([C:49]([O:51][C@H:52]2[C:56]3[N:57]=[CH:58][N:59]=[C:60](Cl)[C:55]=3[C@H:54]([CH3:62])[CH2:53]2)=[O:50])=[CH:47][CH:46]=1)([O-:44])=[O:43]>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].CN(C=O)C>[N+:42]([C:45]1[CH:46]=[CH:47][C:48]([C:49]([O:51][C@H:52]2[C:56]3[N:57]=[CH:58][N:59]=[C:60]([C:31]4[CH:30]=[CH:29][C:28]5[C:24]([CH:14]([C:11]6[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][CH:10]=6)[CH2:15][NH:16][C:17]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:23])=[N:25][S:26][C:27]=5[CH:32]=4)[C:55]=3[C@H:54]([CH3:62])[CH2:53]2)=[O:50])=[CH:63][CH:64]=1)([O-:44])=[O:43]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 67438565Tert-butyl 2-(4-chlorophenyl)-2-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]isothiazol-3-yl)ethylcarbamateHCID 86651804(5R,7R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate

Produkt 1

HCID 67437737HCID 67437737, VerbindungAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 53485975CID 53485975KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

DMF (3 mL) and 2M aqueous Na2CO3 (0.38 mL, 0.76 mmol) were added to a nitrogen flushed flask containing tert-butyl 2-(4-chlorophenyl)-2-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]isothiazol-3-yl)ethylcarbamate (150 mg, 0.291 mmol), (5R,7R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate (117 mg, 0.350 mmol) and dichloro[1,1′-bis(diphenylphosphino)-ferrocene]palladium(II) dichloromethane adduct (12 mg, 0.015 mmol). The mixture was heated at 80° C. for 1 hour. The mixture was cooled to room temperature and partitioned between EtOAc and water. The combined organic layers were washed with saturated aqueous NaHCO3 and brine, dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexanes:EtOAc (4:1 to 1:1) to give (5R,7R)-4-(3-(2-(tert-butoxycarbonylamino)-1-(4-chlorophenyl)ethyl)benzo[d]isothiazol-6-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-yl 4-nitrobenzoate (102 mg, 51%) as an oil. LCMS (APCI+) m/z 630, 632 [M+H]+; Rt=4.68 min.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between EtOAc and water
  3. washThe combined organic layers were washed with saturated aqueous NaHCO3 and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with hexanes:EtOAc (4:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-b17e7973bbe04b6c9e832c64c0804358
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329709B2

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