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Propargyl alcohol → HCID 12083033, Verbindung

HRID 1168508
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1168508
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([Li])CCC.Br[C:26]1[CH:27]=[C:28]2[C:33]3=[C:34]([CH2:36][C:37]([CH3:39])([CH3:38])[N:32]3[CH:31]=[C:30]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:29]2=[O:45])[CH:35]=1.[CH2:46]([OH:49])[C:47]#[CH:48]>C1COCC1.C(NCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu](I)I>[OH:49][CH2:46][C:47]#[C:48][C:26]1[CH:27]=[C:28]2[C:33]3=[C:34]([CH2:36][C:37]([CH3:39])([CH3:38])[N:32]3[CH:31]=[C:30]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:29]2=[O:45])[CH:35]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 7859Propargyl alcoholHCID 11776TriphenylphosphineHCID 12083032ethyl 8-bromo-2,2-dimethyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylateHCID 178418339Butyllithium

Produkt 1

HCID 12083033HCID 12083033, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 83717
Copper iodide
Katalysator
HCID 167845palladium(II) acetateKatalysator
HCID 8021DiethylamineLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

A solution of palladium acetate (73 mg) and triphenyl phosphine (191 mg) in dry THF (6.0 mL) under nitrogen is cooled to 0° C. A solution of n-butyllithium (1.6 M in hexanes, 444 μL) is added dropwise and after 15 min, the solution is warmed to 22° C. for 15 min. The solution is then canulated into a mixture of ethyl 8-bromo-2,2-dimethyl-6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylate (Preparation 13, 350 mg), copper iodide (84 mg) and propargyl alcohol (75 μL) in diethylamine (6.0 mL). The reaction is warmed to 45° C. for 2 hours. The reaction is filtered, diluted with CH2Cl2 (100 mL), and washed with water. The organic layer is dried (MgSO4), filtered, and concentrated. The crude product is chromatographed over silica gel, eluting with 5% MeOH in CHCl3 and recrystallized from EtOAc to afford 229 mg of the title compound as white crystals. Physical characteristics: M.p. 237° C. (dec); 1H NMR (DMSO-d6) δ8.74, 7.81, 7.60, 5.37, 4.33, 4.23, 3.39, 1.63 (s, 6 H), 1.29 (t, J=7 Hz, 3 H); IR (diffuse reflectance) 2391, 2222, 2058, 1921, 1680, 1637, 1595, 1542, 1510, 1317, 1216, 1186, 1040, 1031, 808 cm−1; MS (EI) m/z 325 (M+). HRMS (FAB) m/z 326.1385 (C19H19NO4+H).

Aufarbeitung

  1. temperatureThe reaction is warmed to 45° C. for 2 hours
  2. filtrationThe reaction is filtered
  3. additiondiluted with CH2Cl2 (100 mL)
  4. washwashed with water
  5. dry with materialThe organic layer is dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is chromatographed over silica gel
  9. washeluting with 5% MeOH in CHCl3
  10. customrecrystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-0e66815af6544d0cb65813a957abd6a8
Quelldatensatz
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06624159B2

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