Stannane, tributyl(1-ethoxyethenyl)- → 4-(3-chloro-5-(1-ethoxyvinyl)pyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

HRID 20644

Reaktionsgleichung

Reaktionsgleichung von HRID 20644
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:28])[C:7]=1[NH:8][C:9]1[C:18]2[C:13](=[C:14]([O:21][CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[O:12][C:11](=[O:27])[CH:10]=1.C([Sn](CCCC)(CCCC)[C:34]([O:36][CH2:37][CH3:38])=[CH2:35])CCC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:28][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:34]([O:36][CH2:37][CH3:38])=[CH2:35])[C:7]=1[NH:8][C:9]1[C:18]2[C:13](=[C:14]([O:21][CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[O:12][C:11](=[O:27])[CH:10]=1

Komponenten

5

Edukt 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 248494324-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

Produkt 1

HCID 248494754-(3-chloro-5-(1-ethoxyvinyl)pyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (0.206 g, 0.441 mmol, Example 11), PdCl2(PPh3)2 (31 mg, 0.044 mmol), tributyl(1-ethoxyvinyl)tin (0.20 mL, 0.57 mmol), and toluene (5 mL) was heated at 80° C. under N2 for 4 h. After allowing to cool to rt, the mixture was filtered through Celite and washed with EtOAc. The filtrate was washed with aqueous KF, dried, filtered, concentrated, and purified by silica gel chromatography (0→50% EtOAc/hexanes) to give 4-(3-chloro-5-(1-ethoxyvinyl)pyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.19 (s, 1H), 8.80 (s, 1H), 8.65 (s, 1H), 7.94 (d, 1H), 7.16 (d, 1H), 4.83 (m, 1H), 4.53 (m, 2H), 4.41 (d, 1H), 3.90 (s, 3H), 3.61 (m, 2H), 1.85-1.52 (m, 8H), 0.89 (t, 3H); MS (ESI): 457.1.

Aufarbeitung

  1. temperatureto cool to rt
  2. filtrationthe mixture was filtered through Celite
  3. washwashed with EtOAc
  4. washThe filtrate was washed with aqueous KF
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography (0→50% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ddc9b5bf070a45d4b17954f779411030
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745646B2

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