Potassium Carbonate → HCID 178455334, Verbindung

HRID 389460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389460
[Cl:1][C:2]1[O:12][C:5]2=[C:6]([NH2:11])[N:7]=[CH:8][C:9](I)=[C:4]2[CH:3]=1.[Si:13]([O:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([N:27]2[CH:31]=[C:30](B(O)O)[CH:29]=[N:28]2)[CH2:23][CH2:22]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[Si:13]([O:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([N:27]2[CH:31]=[C:30]([C:9]3[CH:8]=[N:7][C:6]([NH2:11])=[C:5]4[O:12][C:2]([Cl:1])=[CH:3][C:4]=34)[CH:29]=[N:28]2)[CH2:23][CH2:22]1)([C:16]([CH3:19])([CH3:17])[CH3:18])([CH3:15])[CH3:14]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 667601342-Chloro-4-iodofuro[2,3-c]pyridin-7-amineHCID 178455325HCID 178455325, Verbindung

Produkt 1

HCID 178455334HCID 178455334, VerbindungAusbeute 63,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 2-chloro-4-iodo-furo[2,3-c]pyridin-7-ylamine (2 g, 7 mmol), [1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]boronic acid (2.75 g, 8.49 mmol), (1,1′bis-(diphenylphosphino)-ferrocene)palladium dichloride (248 mg, 0.340 mmol) and potassium carbonate (2.35 g, 17.0 mmol) in 1,4-dioxane (20 mL) and water (9.5 mL) was heated to 70° C. for 22 h. The mixture was partitioned between ethyl acetate and water and the aqueous phase extracted with DCM. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. Purification by ISCO chromatography (10% to 50% ethyl acetate:heptane) followed by trituration with ether:heptane afforded 2.0 g (60%) of the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 7.97 (s, 1 H), 7.76-7.69 (m, 1 H), 7.62 (s, 1 H), 6.73 (s, 1 H), 4.73 (s, 2 H), 4.17 (tt, J=3.9, 11.6 Hz, 1 H), 3.73 (tt, J=4.3, 10.5 Hz, 1 H), 2.23 (d, J=12.1 Hz, 2 H), 2.09-1.99 (m, 2 H), 1.91 (dq, J=3.5, 11.9 Hz, 2 H), 1.61-1.48 (m, 2 H), 0.92 (s, 9 H), 0.10 (s, 6 H); MS (ESI): 447.39, 449.35 [M+H]+.

Aufarbeitung

  1. customThe mixture was partitioned between ethyl acetate and water
  2. extractionthe aqueous phase extracted with DCM
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by ISCO chromatography (10% to 50% ethyl acetate:heptane)

Quellen und Nachweise

ORD-Eintrag
ord-449c54b53f4e430eaca457be091cda8c
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378104B2

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