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Cesium carbonate → 7-(3,5-Dimethylisoxazol-4-yl)-4-phenyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

HRID 589093
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 589093
Br[C:2]1[CH:11]=[CH:10][C:9]2[NH:12][C:13](=[O:14])[N:7]3[C:8]=2[C:3]=1[CH2:4][CH2:5][CH:6]3[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.BrC1C=C2C3=C(NC(=O)N3C(C3C=CC=CC=3)CC2)C=1.[CH3:41][C:42]1[C:46](B(O)O)=[C:45]([CH3:50])[O:44][N:43]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.O>[CH3:41][C:42]1[C:46]([C:2]2[CH:11]=[CH:10][C:9]3[NH:12][C:13](=[O:14])[N:7]4[C:8]=3[C:3]=2[CH2:4][CH2:5][CH:6]4[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:45]([CH3:50])[O:44][N:43]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 904091427-Bromo-4-phenyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-oneHCID 904098178-bromo-4-phenyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

Produkt 1

HCID 904098527-(3,5-Dimethylisoxazol-4-yl)-4-phenyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one
Ausbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 7-bromo-4-phenyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (0.050 g, 0.15 mmol) (4.4:1 mixture of isomers with 8-bromo-4-phenyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one as the minor isomer), (3,5-dimethylisoxazol-4-yl)boronic acid (10.7 mg, 0.0759 mmol), and cesium carbonate (99.0 mg, 0.304 mmol) in 1,2-dimethoxyethane (1.21 mL) and water (0.303 mL) was degassed with nitrogen for 5 min. The reaction mixture was treated with PEPPSI-IPr (5.2 mg, 0.0076 mmol) [Aldrich, cat. #669032], degassed with nitrogen for 5 min, and heated at 90° C. for 1 h. The reaction mixture was then diluted with ethyl acetate (25 mL) and water (20 mL). The organic layer was separated, washed with brine, dried over sodium sulfate, filtered, and concentrated to give a crude residue. Purification via preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% trifluoroacetic acid, at flow rate of 60 mL/min) gave the desired product (14.7 mg, 28%) as a racemic mixture. 1H NMR (500 MHz, CDCl3) δ 10.00 (s, 1H), 7.34-7.20 (m, 3H), 7.08-6.95 (m, 3H), 6.88-6.76 (m, 1H), 5.54 (s, 1H), 2.45-1.96 (m, 10H); LCMS calculated for C21H20N3O2 (M+H)+: m/z=346.2. found: 346.1.

Aufarbeitung

  1. customwas degassed with nitrogen for 5 min
  2. customdegassed with nitrogen for 5 min
  3. additionThe reaction mixture was then diluted with ethyl acetate (25 mL) and water (20 mL)
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a crude residue
  10. customPurification via preparative LCMS (XBridge C18 column
  11. washeluting with a gradient of acetonitrile/water containing 0.1% trifluoroacetic acid, at flow rate of 60 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-c4169bb0319d47f59557675aef61d145
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09227985B2

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