Cesium carbonate → HCID 17978962, Verbindung

HRID 1796042

Reaktionsgleichung

Reaktionsgleichung von HRID 1796042
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([C:10]([CH3:14])([CH3:13])[C:11]#[N:12])=[N:6][C:5]=12.Br[C:16]1[N:21]=[C:20]([C:22]2[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=2[C:24]#[N:25])[CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:11]([C:10]([C:7]1[CH:8]=[CH:9][N:4]2[C:3]([C:16]3[N:21]=[C:20]([C:22]4[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=4[C:24]#[N:25])[CH:19]=[CH:18][CH:17]=3)=[CH:2][N:1]=[C:5]2[N:6]=1)([CH3:14])[CH3:13])#[N:12]

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 221807852-(6-Bromopyridin-2-yl)benzonitrileHCID 695602862-(Imidazo[1,2-alpha]pyrimidin-7-yl)-2-methylpropionitrile

Produkt 1

HCID 17978962HCID 17978962, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-(Imidazo[1,2-α]pyrimidin-7-yl)-2-methylpropionitrile (100 mg, 0.51 mmol), 2-(6-bromopyridin-2-yl)benzonitrile (159 mg, 0.61 mmol) and cesium carbonate (332 mg, 1.02 mmol) were suspended in 1,4-dioxane and degassed with nitrogen for 20 min. Tetrakis(triphenylphosphine)-palladium(0) (29 mg, 0.025 mmol) was added and the mixture was heated at 80° C. for 3 h. The reaction was cooled to ambient temperature then diluted with water (60 ml) and extracted with ethyl acetate (2×100 ml). The combined organic extracts were washed with brine (70 ml), dried over anhydrous sodium sulfate, filtered and evaporated to give a pale yellow oil. The oil was purified by chromatography on silica gel eluting with dichloromethane on a gradient of methanol (0-1%). Collecting appropriate fractions followed by recrystallisation from ethyl acetate/isohexane gave 2-{6-[7-(1-cyano-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]pyridin-2-yl}benzonitrile (70 mg, 38%) as a white solid: δH (360 MHz, CDCl3) 1.86 (6H, s), 7.43 (1H, d, J 7), 7.59-7.63 (2H, m), 7.80 (2H, m), 7.86-7.97 (3H, m), 8.42 (1H, s), 10.44 (1H, d, J 7); m/z (ES+) 365 (M++H).

Aufarbeitung

  1. customdegassed with nitrogen for 20 min
  2. temperatureThe reaction was cooled to ambient temperature
  3. extractionextracted with ethyl acetate (2×100 ml)
  4. washThe combined organic extracts were washed with brine (70 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a pale yellow oil
  9. customThe oil was purified by chromatography on silica gel eluting with dichloromethane on a gradient of methanol (0-1%)
  10. customCollecting appropriate fractions
  11. customfollowed by recrystallisation from ethyl acetate/isohexane

Quellen und Nachweise

ORD-Eintrag
ord-9e09d8e8a14b4e67918fd4cc241e8413
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030128B2

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