Cesium carbonate → HCID 59238963, Verbindung

HRID 2060963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2060963
C([N:8]1[C:20]2[C:19]([OH:21])=[C:18]3[N:22](C(OC(C)(C)C)=O)[C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][C:28]=4[C:17]3=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([F:37])[CH:13]=2)(OC(C)(C)C)=O.Br[CH2:39][CH2:40][CH2:41][NH:42]C(=O)OC(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[F:37][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:20]1[C:19]([O:21][CH2:39][CH2:40][CH2:41][NH2:42])=[C:18]3[NH:22][C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][C:28]=4[C:17]3=[CH:16][C:15]2=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 67212243HCID 67212243, Verbindung

Produkt 1

HCID 59238963HCID 59238963, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 5,7-diBOC-2,10-difluoro-6-hydroxyindolo[2,3-b]carbazole (4.03 g, 8.0 mmol), tert-butyl 3-bromopropylcarbamate (2.20 g, 9.2 mmol), and Cs2CO3 (10.0 g, 31 mmol), and anhydrous MeCN (120 mL) was heated at 100° C. under Ar until the starting material disappeared (˜2 h). After cooled to RT, the inorganic salt was removed by filtration, washed with dichloromethane, and the combined filtrate was concentrated. The resulting residue 3-(2,10-difluoro-5,7-diBOC-indolo[2,3-b]carbazol-6-yloxy)propan-1-amine was dissolved in CH2Cl2 (100 mL). TFA (10 mL) was added and the solution was stirred at RT overnight. After evaporation, the residue was subjected to chromatography on silica gel, eluting with ethyl acetate/hexane/MeOH (10% cNH3.H2O) (50/50/10-100/0/10), giving 2.35 g (82%) of 3-(2,10-difluoro-5,7-dihydroindolo[2,3-b]carbazol-6-yloxy)propan-1-amine. 1H NMR (400 MHz, DMSO-d6) δ 11.8 (br s, 2H), 8.56 (s, 1H), 7.89 (dd, J=9.4, 2.6 Hz, 2H), 7.44 (dd, J=8.6, 4.6 Hz, 2H), 7.17 (td, J=9.2, 2.4 Hz, 2H), 4.36 (t, J=6.2 Hz, 2H), 2.97 (t, J=6.2 Hz, 2H), 1.98 (pentalet, J=6.2 Hz, 2H).

Aufarbeitung

  1. custom(˜2 h)
  2. temperatureAfter cooled to RT
  3. customthe inorganic salt was removed by filtration
  4. washwashed with dichloromethane
  5. concentrationthe combined filtrate was concentrated
  6. dissolutionThe resulting residue 3-(2,10-difluoro-5,7-diBOC-indolo[2,3-b]carbazol-6-yloxy)propan-1-amine was dissolved in CH2Cl2 (100 mL)
  7. additionTFA (10 mL) was added
  8. customAfter evaporation
  9. washeluting with ethyl acetate/hexane/MeOH (10% cNH3.H2O) (50/50/10-100/0/10)

Quellen und Nachweise

ORD-Eintrag
ord-069faf33cab945a3980aa1324bdab083
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278341B2

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