Cesium carbonate → 3-methyl-N-[3-(pentafluoroethyl)phenyl]-5-(1,3-thiazol-5-yl)aniline

HRID 1039906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039906
Cl[C:2]1N=[C:6]([C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][N:3]=1.[CH3:15][C:16]1[CH:17]=C([CH:20]=[C:21]([C:23]2[S:27][CH:26]=[N:25][CH:24]=2)[CH:22]=1)N.[CH3:28][C:29]1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=C[C:30]1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:15][C:16]1[CH:17]=[C:2]([CH:20]=[C:21]([C:23]2[S:27][CH:26]=[N:25][CH:24]=2)[CH:22]=1)[NH:3][C:4]1[CH:30]=[CH:29][CH:28]=[C:6]([C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])[CH:5]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 584563653-Methyl-5-(1,3-thiazol-5-yl)anilineHCID 866582362-Chloro-4-(pentafluoroethyl)pyrimidine

Produkt 1

HCID 866582353-methyl-N-[3-(pentafluoroethyl)phenyl]-5-(1,3-thiazol-5-yl)anilineAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 2-chloro-4-(pentafluoroethyl)pyrimidine (61 mg, 0.26 mmol) and 3-methyl-5-(1,3-thiazol-5-yl)aniline (50 mg, 0.26 mmol) in degassed 1,4-dioxane (1.1 mL) were added Xantphos (23 mg, 0.039 mmol), Pd(OAc)2 (5.9 mg, 0.026 mmol) and Cs2CO3 (172 mg, 0.53 mmol) and the reaction was heated to 100° C. for 30 minutes. After cooling, the reaction was partitioned between EtOAc (10 mL) and saturated aqueous sodium bicarbonate. The layers were separated and the aqueous phase was extracted EtOAc (10 mL). The combined organic phases were washed with saturated aqueous sodium chloride (10 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Purification on silica (20-60% ethyl acetate in hexanes) afforded 3-methyl-N-[3-(pentafluoroethyl)phenyl]-5-(1,3-thiazol-5-yl)aniline (13 mg, 13%) as a colorless foam. MS ESI: [M+H]+ m/z 387.0.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe reaction was partitioned between EtOAc (10 mL) and saturated aqueous sodium bicarbonate
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted EtOAc (10 mL)
  5. washThe combined organic phases were washed with saturated aqueous sodium chloride (10 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification on silica (20-60% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-dcad3f042072443ca4bed0e8137b1bb5
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551984B2

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