Sodium Carbonate → HCID 178508357, Verbindung

HRID 1909930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1909930
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][C:10]([N:12]1[C:20]2[C:15](=[CH:16][C:17]([C:21]3[C:25]4[C:26]([NH2:31])=[N:27][CH:28]=[C:29](I)[C:24]=4[S:23][CH:22]=3)=[CH:18][CH:19]=2)[CH2:14][CH2:13]1)=[O:11].[NH:32]1[CH:36]=[CH:35][C:34](B(O)O)=[N:33]1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C(OCC)(=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][C:10]([N:12]1[C:20]2[C:15](=[CH:16][C:17]([C:21]3[C:25]4[C:26]([NH2:31])=[N:27][CH:28]=[C:29]([C:36]5[CH:35]=[CH:34][NH:33][N:32]=5)[C:24]=4[S:23][CH:22]=3)=[CH:18][CH:19]=2)[CH2:14][CH2:13]1)=[O:11]

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 668236633-{1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-iodothieno[3,2-c]pyridin-4-amineHCID 178514837HCID 178514837, Verbindung

Produkt 1

HCID 178508357HCID 178508357, VerbindungAusbeute 35,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a 25 mL microwave reactor vial was charged 3-{1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-iodothieno[3,2-c]pyridin-4-amine (150 mg, 0.274 mmol), 1H-pyrazol-3-ylboronic acid (30.7 mg, 0.274 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (11.19 mg, 0.014 mmol), and sodium carbonate (58.1 mg, 0.548 mmol) followed by dioxane (5 mL), and water (1 mL). The reaction was heated at 120° C. for 30 min in microwave reactor. Ethyl acetate (20 mL) was added and the layers were separated. The organic layer was washed with brine, concentrated, and the residue purified by silica gel chromatography (0%-100% EtOAc in hexanes). Product came out at 100% EtOAc in 5 minutes, the fractions with the product were combined and evaporated to dryness to afford the title compound as a light gray solid (48 mg). LC/MS (ES) m/z=488.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.99 (s, 1H) 8.36 (s, 1H) 8.12 (d, J=8.1 Hz, 1H) 7.85 (s, 1H) 7.48 (s, 1H) 7.38 (s, 1H) 7.14-7.31 (m, 4H) 6.84 (s, 1H) 5.50 (br. s., 2H) 4.32 (t, J=8.5 Hz, 2H) 3.96 (s, 2H) 3.25-3.32 (m, 2H).

Aufarbeitung

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. concentrationconcentrated
  4. customthe residue purified by silica gel chromatography (0%-100% EtOAc in hexanes)
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-ab168c115df4493790c33abab2061abb
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598156B2

Notizen zur Reaktion

Wird geladen…