Potassium Carbonate → (4-Methyl-pyridin-2-yl)-[6-(2-phenyl-oxazol-5-yl)-pyridin-2-yl]-amine

HRID 1854613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1854613
I[C:2]1[O:3][C:4]([C:7]2[N:12]=[C:11]([NH:13][C:14]3[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=3)[CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:20][C:18]1[CH:17]=[CH:16][N:15]=[C:14]([NH:13][C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:4]3[O:3][C:2]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:6][CH:5]=3)[N:12]=2)[CH:19]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 53311312HCID 53311312, Verbindung

Produkt 1

HCID 67323426(4-Methyl-pyridin-2-yl)-[6-(2-phenyl-oxazol-5-yl)-pyridin-2-yl]-amineAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of [6-(2-iodo-oxazol-5-yl)-pyridin-2-yl]-(4-methyl-pyridin-2-yl)-amine (46 mg, 0.121 mmol), phenylboronic acid (30 mg, 0.246 mmol), K2CO3 (37 mg, 0.268 mmol) and Pd(PPh3)4 (14 mg, 0.012 mmol) in a mixture of THF (4 ml) and water (2 ml) was stirred at 90° C. for 18 h. The cooled reaction mixture was treated with water and extracted with EtOAc. The combined organics were dried over MgSO4, filtered and evaporated under reduced pressure before purification by column chromatography on SiO2 eluting with 30% EtOAc in cyclohexane to afford the title compound as a pale orange solid (30 mg, 75%). 1H NMR (DMSO-d6, 300 MHz): δ=9.79 (s, 1H), 8.12 (m, 2H), 8.02 (s, 1H), 7.93 (s, 1H), 7.86 (s, 1H), 7.78 (m, 2H), 7.58 (m, 2H), 7.40 (t, J=7.0 Hz, 1H), 7.33 (t, J=7.0 Hz, 1H), 6.78 (d, J=5.0 Hz, 1H), 2.37 (s, 3H). (ESI+) m/z 329 (M+H)+. Retention time=2.84 mins (method 1).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure before purification by column chromatography on SiO2 eluting with 30% EtOAc in cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-08c93b4c861441d9b5e1b1c3c16c3d19
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962665B2

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